Method for treating a disease related to the glucocorticoid receptor

ABSTRACT

A method for treating a disease related to the glucocorticoid receptor involving administering a pharmacologically effective amount of a 1,2-hydroquinoline compound.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation application of application Ser. No.12/312,392 filed May 7, 2009 (U.S. Pat. No. 8,008,496), which is theUnited States national phase application under 35 USC 371 ofInternational application PCT/JP2007/072081 filed Nov. 14, 2007. Theentire contents of each of application Ser. No. 12/312,392 andInternational application PCT/JP2007/072081 are hereby incorporated byreference herein.

TECHNICAL FIELD

The present invention relates to novel 1,2-dihydroquinoline derivativeshaving substituted phenylchalcogeno lower alkyl group andester-introduced phenyl group as substituents or a salt thereof, whichare useful as pharmaceuticals. The derivatives have a glucocorticoidreceptor binding activity and are useful as glucocorticoid receptormodulators having a nonsteroidal structure (glucocorticoid receptoragonists and/or glucocorticoid receptor antagonists).

BACKGROUND ART

A glucocorticoid receptor is a 94 kDa ligand-activated intracellulartranscriptional regulatory factor that is a member of the nuclearreceptor superfamily. This receptor is known to affect the regulation ofthe metabolism of carbohydrates, proteins, fats and the like,suppression of the immune or inflammatory responses, activation of thecentral nervous system, regulation of cardiovascular function, and basaland stress-related homeostasis and the like due to its transcriptionalregulatory action. As diseases which are considered to be related toglucocorticoid receptor, metabolic disorders such as diabetes andobesity, inflammatory diseases such as enteritis and chronic obstructivepulmonary diseases, autoimmune diseases such as connective tissuediseases, allergic diseases such as asthma, atopic dermatitis andallergic rhinitis, central nervous system diseases such as psychiatricdisorders, Alzheimer's disease and drug use disorders, cardiovasculardiseases such as hypertension, hypercalcemia, hyperinsulinemia andhyperlipidemia, homeostasis-related diseases causing an abnormality ofneuro-immune-endocrine balance, glaucoma and the like are known (SOUGOURINSYOU, 54(7), 1951-2076 (2005), JP-A-2002-193955). Therefore, acompound having a glucocorticoid receptor binding activity is useful asa preventive and/or therapeutic agent for these diseases.

As such a compound having a glucocorticoid receptor binding activity,glucocorticoid receptor agonists synthesized in the living body such ascortisol and corticosterone, synthetic glucocorticoid receptor agonistssuch as dexamethasone, prednisone and prednisilone, non-selectiveglucocorticoid receptor antagonists such as RU486 and the like are known(JP-A-2002-193955).

On the other hand, compounds having a 1,2-dihydroquinoline structure aredisclosed as steroid receptor modulators in WO 2004/018429,JP-T-10-0510840, WO 2006/019716 and the like. In WO 2004/018429,JP-T-10-0510840 and WO 2006/019716, many compounds which have very broadand a variety of chemical structures are disclosed, and1,2-dihydroquinoline structure is disclosed as one of them. However,1,2-dihydroquinoline derivatives having substituted phenylchalcogenolower alkyl group and ester-introduced phenyl group as substituents havenot been specifically disclosed at all.

DISCLOSURE OF THE INVENTION Problems to be Solved

It is a very interesting subject to study the synthesis of novel1,2-dihydroquinoline derivatives having substituted phenylchalcogenolower alkyl group and ester-introduced phenyl group as substituents or asalt thereof, and to find a pharmacological action of the derivatives ora salt thereof.

Means of Solving Problems

The present inventors conducted the studies of the synthesis of novel1,2-dihydroquinoline derivatives having substituted phenylchalcogenolower alkyl group and ester-introduced phenyl group as substituents or asalt thereof having a novel chemical structure, and succeeded inproducing a large number of novel compounds.

These novel compounds have chemical structural features 1) to 3) shownin below.

1) Having an ester structure (X is —C(O)—, —C(O)NR⁸—, —S(O)— or —S(O)₂—)in A part of the general formula (1).

2) Having a hydroxy group or a lower alkoxy group in B part of thegeneral formula (1).

3) Having a substituted phenylchalcogeno lower alkyl group (Z is achalcogen atom, that is an oxygen atom, a sulfur atom or the like, Y isa lower alkylene group) in C part of the general formula (1).

Further, as a result of the study about the pharmacological actions ofthe novel compounds, the present inventors found that the novelcompounds have a glucocorticoid receptor binding activity and are usefulas pharmaceuticals, and thus the present invention has been completed.

That is, the present invention relates to compounds represented by thefollowing general formula (1) or a salt thereof (hereinafter referred toas “the present compound”) and a pharmaceutical composition containingthe same. Further, a preferred invention in its pharmaceutical userelates to glucocorticoid receptor modulators, and its target diseasesare considered to be glucocorticoid receptor-related diseases, that is,metabolic disorders such as diabetes and obesity, inflammatory diseasessuch as enteritis and chronic obstructive pulmonary diseases, autoimmunediseases such as connective tissue diseases, allergic diseases such asasthma, atopic dermatitis and allergic rhinitis, central nervous systemdiseases such as psychiatric disorders, Alzheimer's disease and drug usedisorders, cardiovascular diseases such as hypertension, hypercalcemia,hyperinsulinemia and hyperlipidemia, homeostasis-related diseasescausing an abnormality of neuro-immune-endocrine balance, glaucoma andthe like, and an invention relating to a preventive or a therapeuticagent for these diseases is particularly preferred.

[R¹ represents a hydrogen atom or a lower alkyl group;

R² represents a hydrogen atom or a lower alkyl group;

R³ and R⁴ may be the same or different and represent a hydrogen atom ora lower alkyl group;

R⁵ represents a hydrogen atom or a lower alkyl group;

R⁶ represents a halogen atom, a lower alkyl group, a hydroxy group, alower alkoxy group, a nitro group or a cyano group;

X represents —C(O)—, —C(O)NR⁸—, —S(O)— or —S(O)₂—;

R⁷ and/or R⁸ may be the same or different and represent a hydrogen atom,a lower alkyl group which may have a substituent, a lower alkenyl groupwhich may have a substituent, a lower alkynyl group which may have asubstituent, a lower cycloalkyl group which may have a substituent, anaryl group which may have a substituent, a heterocyclic group which mayhave a substituent, a lower alkoxy group which may have a substituent, alower alkenyloxy group which may have a substituent, a lower alkynyloxygroup which may have a substituent, a lower cycloalkyloxy group whichmay have a substituent, an aryloxy group which may have a substituent ora heterocyclic oxy group which may have a substituent;

Y represents a lower alkylene group;

Z represents a chalcogen atom;

p represents 0, 1, 2 or 3, in the case where p is 2 or 3, each R⁶ may bethe same or different. Hereinafter the same shall apply.]

Advantage of the Invention

The present invention provides novel 1,2-dihydroquinoline derivativeshaving substituted phenylchalcogeno lower alkyl group andester-introduced phenyl group as substituents or a salt, which areuseful as pharmaceuticals. The present compound has an excellentglucocorticoid receptor binding activity and is useful as aglucocorticoid receptor modulator. In particular, the present compoundis useful as a preventive or therapeutic agent for glucocorticoidreceptor-related diseases, that is, metabolic disorders such as diabetesand obesity, inflammatory diseases such as enteritis and chronicobstructive pulmonary diseases, autoimmune diseases such as connectivetissue diseases, allergic diseases such as asthma, atopic dermatitis andallergic rhinitis, central nervous system diseases such as psychiatricdisorders, Alzheimer's disease and drug use disorders, cardiovasculardiseases such as hypertension, hypercalcemia, hyperinsulinemia andhyperlipidemia, homeostasis-related diseases causing an abnormality ofneuro-immune-endocrine balance, glaucoma and the like.

BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, definitions of terms and phrases (atoms, groups and thelike) used in this specification will be described in detail. Inaddition, when the definition of terms and phrases is applied to thedefinition of another terms and phrases, a desirable range and theparticularly desirable range of each definition is also applied.

The “chalcogen atom” refers to a oxygen or sulfur atom.

The “halogen atom” refers to a fluorine, chlorine, bromine or iodineatom.

The “lower alkyl group” refers to a straight chain or branched alkylgroup having 1 to 8 carbon atoms, preferably 1 to 6, especiallypreferably 1 to 4. Specific examples thereof include methyl, ethyl,n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, isopropyl,isobutyl, sec-butyl, tert-butyl and isopentyl groups and the like.

The “lower alkenyl group” refers to a straight chain or branched alkenylgroup having 2 to 8 carbon atoms, preferably 2 to 6, especiallypreferably 2 to 4. Specific examples thereof include vinyl, propenyl,butenyl, pentenyl, hexenyl, heptenyl, octenyl, isopropenyl,2-methyl-1-propenyl and 2-methyl-2-butenyl groups and the like.

The “lower alkynyl group” refers to a straight chain or branched alkynylgroup having 2 to 8 carbon atoms, preferably 2 to 6, especiallypreferably 2 to 4. Specific examples thereof include ethynyl, propynyl,butynyl, pentynyl, hexynyl, heptynyl, octynyl, isobutynyl andisopentynyl groups and the like.

The “lower cycloalkyl group” refers to a cycloalkyl group having 3 to 10carbon atoms, preferably 3 to 8, especially preferably 3 to 6. Specificexamples thereof include cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, cyclononanyl and cyclodecanylgroups.

The “aryl group” refers to a residue formed by removing one hydrogenatom from a monocyclic aromatic hydrocarbon group, or bicyclic ortricyclic condensed polycyclic aromatic hydrocarbon having 6 to 14carbon atoms. Specific examples thereof include phenyl, naphthyl,anthryl and phenanthryl groups and the like.

The “heterocyclic ring” refers to a saturated or unsaturated monocyclicheterocyclic ring having one or a plurality of heteroatoms selected froma nitrogen atom, an oxygen atom and a sulfur atom in the ring(preferably, a saturated or unsaturated monocyclic 5 or 6 memberedheterocyclic ring having one or two heteroatoms and 3 to 5 carbon atomsin the ring), or a bicyclic or tricyclic condensed polycyclicheterocyclic ring (preferably, a bicyclic or tricyclic condensedpolycyclic heterocyclic ring having one or two heteroatoms and 7 to 13carbon atoms in the ring).

Specific examples of the “saturated monocyclic heterocyclic ring”include pyrrolidine, pyrazolidine, imidazolidine, triazolidine,piperidine, hexahydropyridazine, hexahydropyrimidine, piperazine,homopiperidine and homopiperazine rings and the like having at least anitrogen atom in the ring, tetrahydrofuran and tetrahydropyran rings andthe like having at least an oxygen atom in the ring, tetrahydrothiopheneand tetrahydrothiopyran rings and the like having a sulfur atom in thering, oxazolidine, isoxazolidine and morpholine rings and the likehaving a nitrogen atom and an oxygen atom in the ring, and thiazolidine,isothiazolidine and thiomorpholine rings and the like having a nitrogenatom and a sulfur atom in the ring.

Further, such a saturated monocyclic heterocyclic ring can be condensedwith a benzene ring or the like to form a bicyclic or tricycliccondensed polycyclic heterocyclic ring such as a dihydroindole,dihydroindazole, dihydrobenzimidazole, tetrahydroquinoline,tetrahydroisoquinoline, tetrahydrocinnoline, tetrahydrophthalazine,tetrahydroquinazoline, tetrahydroquinoxaline, dihydrobenzofuran,dihydroisobenzofuran, chromane, isochromane, dihydrobenzothiophene,dihydroisobenzothiophene, thiochromane, isothiochromane,dihydrobenzoxazole, dihydrobenzisoxazole, dihydrobenzoxazine,dihydrobenzothiazole, dihydrobenzisothiazole, dihydrobenzothiazine,xanthene, 4a-carbazole, or perimidine ring and the like.

Specific examples of the “unsaturated monocyclic heterocyclic ring”include dihydropyrrole, pyrrole, dihydropyrazole, pyrazole,dihydroimidazole, imidazole, dihydrotriazole, triazole,tetrahydropyridine, dihydropyridine, pyridine, tetrahydropyridazine,dihydropyridazine, pyridazine, tetrahydropyrimidine, dihydropyrimidine,pyrimidine, tetrahydropyrazine, dihydropyrazine and pyrazine rings andthe like having at least a nitrogen atom in the ring, dihydrofuran,furan, dihydropyran and pyran rings and the like having at least anoxygen atom in the ring, dihydrothiophene, thiophene, dihydrothiopyranand thiopyran rings and the like having a sulfur atom in the ring,dihydrooxazole, oxazole, dihydroisoxazole, isoxazole, dihydrooxazine andoxazine rings and the like having a nitrogen atom and an oxygen atom inthe ring, dihydrothiazole, thiazole, dihydroisothiazole, isothiazole,dihydrothiazine and thiazine rings and the like having a nitrogen atomand a sulfur atom in the ring.

Further, such an unsaturated monocyclic heterocyclic ring can becondensed with a benzene ring or the like to form a bicyclic ortricyclic condensed polycyclic heterocyclic ring such as an indole,indazole, benzimidazole, benzotriazole, dihydroquinoline, quinoline,dihydroisoquinoline, isoquinoline, phenanthridine, dihydrocinnoline,cinnoline, dihydrophthalazine, phthalazine, dihydroquinazoline,quinazoline, dihydroquinoxaline, quinoxaline, benzofuran, isobenzofuran,chromene, isochromene, benzothiophene, isobenzothiophene, thiochromene,isothiochromene, benzoxazole, benzisoxazole, benzoxazine, benzothiazole,benzisothiazole, benzothiazine, phenoxanthin, carbazole, β-carboline,phenanthridine, acridine, phenanthroline, phenazine, phenothiazine orphenoxazine ring and the like.

Incidentally, among the above “heterocyclic ring”, “monocyclicheterocyclic ring” is defined as the thing which put saturatedmonocyclic heterocyclic ring and unsaturated monocyclic heterocyclicring together.

The “heterocyclic group” refers to a residue formed by removing ahydrogen atom from heterocyclic ring mentioned above.

The “lower alkoxy group” refers to a group formed by replacing thehydrogen atom of a hydroxy group with a lower alkyl group. Specificexamples thereof include methoxy, ethoxy, n-propoxy, n-butoxy,n-pentoxy, n-hexyloxy, n-heptyloxy, n-octyloxy, isopropoxy, isobutoxy,sec-butoxy, tert-butoxy and isopentoxy groups and the like.

The “lower alkenyloxy group” refers to a group formed by replacing thehydrogen atom of a hydroxy group with a lower alkenyl group. Specificexamples thereof include vinyloxy, propenyloxy, butenyloxy, pentenyloxy,hexenyloxy, heptenyloxy, octenyloxy, isopropenyloxy,2-methyl-1-propenyloxy and 2-methyl-2-butenyloxy groups and the like.

The “lower alkynyloxy group” refers to a group formed by replacing thehydrogen atom of a hydroxy group with a lower alkynyl group. Specificexamples thereof include ethynyloxy, propynyloxy, butynyloxy,pentynyloxy, hexynyloxy, heptynyloxy, octynyloxy, isobutynyloxy andisopentynyloxy groups and the like.

The “lower cycloalkyloxy group” refers to a group formed by replacingthe hydrogen atom of a hydroxy group with a lower cycloalkyl group.Specific examples thereof include cyclopropyloxy, cyclobutyloxy,cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, cyclooctyloxy,cyclononanyloxy and cyclodecanyloxy groups.

The “aryloxy group” refers to a group formed by replacing the hydrogenatom of a hydroxy group with an aryl group. Specific examples thereofinclude phenoxy, naphthoxy, anthryloxy and phenanthryloxy groups and thelike.

The “heterocyclic oxy group” refers to a group formed by replacing thehydrogen atom of a hydroxy group with a heterocyclic group.

The “lower alkylthio group” refers to a group formed by replacing thehydrogen atom of a mercapto group with a lower alkyl group. Specificexamples thereof include methylthio, ethylthio, n-propylthio,n-butylthio, n-pentylthio, n-hexylthio, n-heptylthio, n-octylthio,isopropylthio, isobutylthio, sec-butylthio, tert-butylthio andisopentylthio groups and the like.

The “lower alkenylthio group” refers to a group formed by replacing thehydrogen atom of a mercapto group with a lower alkenyl group. Specificexamples thereof include vinylthio, propenylthio, butenylthio,pentenylthio, hexenylthio, heptenylthio, octenylthio, isopropenylthio,2-methyl-1-propenylthio and 2-methyl-2-butenylthio groups and the like.

The “lower alkynylthio group” refers to a group formed by replacing thehydrogen atom of a mercapto group with a lower alkynyl group. Specificexamples thereof include ethynylthio, propynylthio, butynylthio,pentynylthio, hexynylthio, heptynylthio, octynylthio, isobutynylthio andisopentynylthio groups and the like.

The “lower cycloalkylthio group” refers to a group formed by replacingthe hydrogen atom of a mercapto group with a lower cycloalkyl group.Specific examples thereof include cyclopropylthio, cyclobutylthio,cyclopentylthio, cyclohexylthio, cycloheptylthio and cyclooctylthiogroups.

The “arylthio group” refers to a group formed by replacing the hydrogenatom of a mercapto group with an aryl group. Specific examples thereofinclude phenylthio, naphthylthio, anthrylthio and phenanthrylthio groupsand the like.

The “heterocyclic thio group” refers to a group formed by replacing thehydrogen atom of a mercapto group with a heterocyclic group.

The “lower alkylcarbonyl group” refers to a group formed by replacingthe hydrogen atom of a formyl group with a lower alkyl group. Specificexamples thereof include methylcarbonyl, ethylcarbonyl,n-propylcarbonyl, n-butylcarbonyl, n-pentylcarbonyl, n-hexylcarbonyl,n-heptylcarbonyl, n-octylcarbonyl, isopropylcarbonyl, isobutylcarbonyl,sec-butylcarbonyl, tert-butylcarbonyl and isopentylcarbonyl groups andthe like.

The “arylcarbonyl group” refers to a group formed by replacing thehydrogen atom of a formyl group with an aryl group. Specific examplesthereof include phenylcarbonyl, naphthylcarbonyl, anthrylcarbonyl andphenanthrylcarbonyl groups and the like.

The “lower alkoxycarbonyl group” refers to a group formed by replacingthe hydrogen atom of a formyl group with a lower alkoxy group. Specificexamples thereof include methoxycarbonyl, ethoxycarbonyl,n-propoxycarbonyl, n-butoxycarbonyl, n-pentoxycarbonyl,n-hexyloxycarbonyl, n-heptyloxycarbonyl, n-octyloxycarbonyl,isopropoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl,tert-butoxycarbonyl and isopentoxycarbonyl groups and the like.

The “aryloxycarbonyl group” refers to a group formed by replacing thehydrogen atom of a formyl group with an aryloxy group. Specific examplesthereof include phenoxycarbonyl, naphthoxycarbonyl, anthryloxycarbonyland phenanthryloxycarbonyl groups and the like.

The “lower alkylcarbonyloxy group” refers to a group formed by replacingthe hydrogen atom of a hydroxy group with a lower alkylcarbonyl group.Specific examples thereof include methylcarbonyloxy, ethylcarbonyloxy,n-propylcarbonyloxy, n-butylcarbonyloxy, n-pentylcarbonyloxy,n-hexylcarbonyloxy, n-heptylcarbonyloxy, n-octylcarbonyloxy,isopropylcarbonyloxy, isobutylcarbonyloxy, sec-butylcarbonyloxy,tert-butylcarbonyloxy and isopentylcarbonyloxy groups and the like.

The “arylcarbonyloxy group” refers to a group formed by replacing thehydrogen atom of a hydroxy group with an arylcarbonyl group. Specificexamples thereof include phenylcarbonyloxy, naphthylcarbonyloxy,anthrylcarbonyloxy and phenanthrylcarbonyloxy groups and the like.

The “lower alkylene group” refers to a straight chain or branchedalkylene group having 1 to 8 carbon atoms, preferably 1 to 6, especiallypreferably 1 to 4. Specific examples thereof include methylene,ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene,heptamethylene, octamethylene, methylmethylene and ethylmethylene groupsand the like.

The “halogenated lower alkyl group” refers to a group formed byreplacing the hydrogen atom of a lower alkyl group with one or aplurality of halogen atoms. Specific examples thereof includedifluoromethyl, trifluoromethyl, trifluoroethyl, trifluoropropyl,dichloromethyl, trichloromethyl, trichloroethyl, trichloropropyl and thelike.

The “halogenated lower alkoxy group” refers to a group formed byreplacing the hydrogen atom of a lower alkoxy group with one or aplurality of halogen atoms. Specific examples thereof includedifluoromethoxy, trifluoromethoxy, trifluoroethoxy, trifluoropropoxy,dichloromethoxy, trichloromethoxy, trichloroethoxy, trichloropropoxy andthe like.

The “lower alkyl group which may have a substituent”, “lower alkenylgroup which may have a substituent”, “lower alkynyl group which may havea substituent”, “lower alkoxy group which may have a substituent”,“lower alkenyloxy group which may have a substituent” and/or “loweralkynyloxy group which may have a substituent” refer to a “lower alkylgroup”, a “lower alkenyl group”, a “lower alkynyl group”, a “loweralkoxy group”, a “lower alkenyloxy group” and/or a “lower alkynyloxygroup” which may have one or a plurality of substituents selected fromthe following α¹ group, preferred one or a plurality of substituentsselected from the following α² group, respectively.

[α¹ Group]

A halogen atom, a lower cycloalkyl group, an aryl group, a heterocyclicgroup, a hydroxy group, a lower alkoxy group, a halogenated lower alkoxygroup, a lower alkenyloxy group, a lower alkynyloxy group, a lowercycloalkyloxy group, an aryloxy group, a heterocyclic oxy group, amercapto group, a lower alkylthio group, a lower alkenylthio group, alower alkynylthio group, a lower cycloalkylthio group, an arylthiogroup, a heterocyclic thio group, a formyl group, a lower alkylcarbonylgroup, an arylcarbonyl group, a carboxy group, a lower alkoxycarbonylgroup, an aryloxycarbonyl group, a lower alkylcarbonyloxy group, anarylcarbonyloxy group, —NR^(a)R^(b), a nitro group and a cyano group.

[α² Group]

A halogen atom, a lower cycloalkyl group, an aryl group, a heterocyclicgroup, a hydroxy group, a lower alkoxy group, a lower alkenyloxy group,a lower alkynyloxy group, a lower cycloalkyloxy group, an aryloxy group,a heterocyclic oxy group and —NR^(a)R^(b).

The “lower cycloalkyl group which may have a substituent”, “aryl groupwhich may have a substituent”, “heterocyclic group which may have asubstituent”, “lower cycloalkyloxy group which may have a substituent”,“aryloxy group which may have a substituent” and/or “heterocyclic oxygroup which may have a substituent” refer to a “lower cycloalkyl group”,an “aryl group”, a “heterocyclic group”, a “lower cycloalkyloxy group”,an “aryloxy group” and/or a “heterocyclic oxy group” which may have oneor a plurality of substituents selected from the following β group,respectively.

[β Group]

A halogen atom, a lower alkyl group, a halogenated lower alkyl group, alower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, anaryl group, a heterocyclic group, a hydroxy group, a lower alkoxy group,a halogenated lower alkoxy group, a lower alkenyloxy group, a loweralkynyloxy group, a lower cycloalkyloxy group, an aryloxy group, aheterocyclic oxy group, a mercapto group, a lower alkylthio group, alower alkenylthio group, a lower alkynylthio group, a lowercycloalkylthio group, an arylthio group, a heterocyclic thio group, aformyl group, a lower alkylcarbonyl group, an arylcarbonyl group, acarboxy group, a lower alkoxycarbonyl group, an aryloxycarbonyl group, alower alkylcarbonyloxy group, an arylcarbonyloxy group, —NR^(a)R^(b), anitro group and a cyano group.

R^(a) and R^(b) in the above “—NR^(a)R^(b)” may be the same or differentand represent a substituent selected from the following γ¹ group,preferably the following γ² group.

[γ¹ Group]

A hydrogen atom, a lower alkyl group, a lower alkenyl group, a loweralkynyl group, a lower cycloalkyl group, an aryl group, a heterocyclicgroup, a lower alkoxycarbonyl group and an aryloxycarbonyl group.

[γ² Group]

A hydrogen atom, a lower alkyl group, an aryl group, a heterocyclicgroup, a lower alkoxycarbonyl group and an aryloxycarbonyl group.

The term “a plurality of groups” as used in this invention means thateach group may be the same or different and stands for 2 or more but notmore than the number of groups which can be introduced intosubstitutable position(s), and the number is preferably 2 or 3, and 2 isparticularly preferable.

Further, in this invention, a hydrogen atom and a halogen atom are alsoincluded in the concept of the “group”.

The “substituted phenylchalcogeno lower alkyl group” as used hereinrefers to a group that a substituted phenyl group binds to a lower alkylgroup through a chalcogen atom.

The “glucocorticoid receptor modulator” as used herein refers to amodulator that exhibits a pharmaceutical action by binding toglucocorticoid receptor. Examples thereof include glucocorticoidreceptor agonists, glucocorticoid receptor antagonists and the like.

The “salt” of the present compound is not particularly limited as longas it is a pharmaceutically acceptable salt. Examples thereof includesalts with an inorganic acid such as hydrochloric acid, hydrobromicacid, hydroiodic acid, nitric acid, sulfuric acid, phosphoric acid orthe like; salts with an organic acid such as acetic acid, fumaric acid,maleic acid, succinic acid, citric acid, tartaric acid, adipic acid,gluconic acid, glucoheptonic acid, glucuronic acid, terephthalic acid,methanesulfonic acid, lactic acid, hippuric acid, 1,2-ethanedisulfonicacid, isethionic acid, lactobionic acid, oleic acid, pamoic acid,polygalacturonic acid, stearic acid, tannic acid,trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonicacid, lauryl sulfate ester, methyl sulfate, naphthalenesulfonic acid,sulfosalicylic acid or the like; quaternary ammonium salts with methylbromide, methyl iodide or the like; salts with a halogen ion such as abromine ion, a chlorine ion, an iodine ion or the like; salts with analkali metal such as lithium, sodium, potassium or the like; salts withan alkaline earth metal such as calcium, magnesium or the like; saltswith a metal such as iron, zinc or the like; salts with ammonia; saltswith an organic amine such as triethylenediamine, 2-aminoethanol,2,2-iminobis(ethanol), 1-deoxy-1-(methylamino)-2-D-sorbitol,2-amino-2-(hydroxymethyl)-1,3-propanediol, procaine,N,N-bis(phenylmethyl)-1,2-ethanediamine or the like.

In the case where there are geometrical isomers and/or optical isomersin the present compound, these isomers are also included in the scope ofthe present invention.

In the case where there are proton tautomers in the present compound,these tautomers (keto-form, enol-form) are also included in the scope ofthe present invention.

In the case where there are hydrate and/or solvate in the presentcompound, these hydrate and/or solvate are also included in the scope ofthe present invention.

In the case where there are polymorphism and polymorphism group(polymorphism system) in the present compound, these polymorphism andpolymorphism group (polymorphism system) are also included in the scopeof the present invention. “Polymorphism group (polymorphism system)”herein means each crystal form in each step where the crystal formchanges depending on conditions and states (the states also include astate of drug formulation) of manufacture, crystallization andpreservation and the like, and the entire process.

(a) Preferred examples of the present compound include compounds inwhich the respective groups are groups as defined below and saltsthereof in the compounds represented by the general formula (1) andsalts thereof.

(a1) R¹ represents a hydrogen atom or a lower alkyl group; and/or

(a2) R² represents a hydrogen atom or a lower alkyl group; and/or

(a3) R³ and R⁴ may be the same or different and represent a hydrogenatom or a lower alkyl group; and/or

(a4) R⁵ represents a hydrogen atom or a lower alkyl group; and/or

(a5) R⁶ represents a halogen atom, a lower alkyl group, a hydroxy group,a lower alkoxy group, a nitro group or a cyano group; and/or

(a6) X represents —CO—, —C(O)NR⁸—, —S(O)— or —S(O)₂—; and/or

(a7) R⁷ and/or R⁸ may be the same or different and represent a hydrogenatom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group,a lower cycloalkyl group, an aryl group, a heterocyclic group, a loweralkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, alower cycloalkyloxy group, an aryloxy group or a heterocyclic oxy group;

in the case where R⁷ and/or R⁸ is a lower alkyl group, a lower alkenylgroup, a lower alkynyl group, a lower alkoxy group, a lower alkenyloxygroup or a lower alkynyloxy group, the lower alkyl group, lower alkenylgroup, lower alkynyl group, lower alkoxy group, lower alkenyloxy groupor lower alkynyloxy group may have one or a plurality of groups selectedfrom a halogen atom, a lower cycloalkyl group, an aryl group, aheterocyclic group, a hydroxy group, a lower alkoxy group, a loweralkenyloxy group, a lower alkynyloxy group, a lower cycloalkyloxy group,an aryloxy group, a heterocyclic oxy group and —NR^(a)R^(b) assubstituent(s);

in the case where R⁷ and/or R⁸ is a lower cycloalkyl group, an arylgroup, a heterocyclic group, a lower cycloalkyloxy group, an aryloxygroup or a heterocyclic oxy group, the lower cycloalkyl group, arylgroup, heterocyclic group, lower cycloalkyloxy group, aryloxy group orheterocyclic oxy group may have one or a plurality of groups selectedfrom a halogen atom, a lower alkyl group, a halogenated lower alkylgroup, an aryl group, a lower alkenyl group, a lower alkynyl group, alower cycloalkyl group, an aryl group, a heterocyclic group, a hydroxygroup, a lower alkoxy group, a halogenated lower alkoxy group, a loweralkenyloxy group, a lower alkynyloxy group, a lower cycloalkyloxy group,an aryloxy group, a heterocyclic oxy group, a mercapto group, a loweralkylthio group, a lower alkenylthio group, a lower alkynylthio group, alower cycloalkylthio group, an arylthio group, a heterocyclic thiogroup, a lower alkylcarbonyl group, an arylcarbonyl group, a loweralkoxycarbonyl group, an aryloxycarbonyl group, a lower alkylcarbonyloxygroup, an arylcarbonyloxy group, —NR^(a)R^(b), a nitro group and a cyanogroup as substituent(s);

R^(a) and R^(b) may be the same or different and represent a hydrogenatom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group,a lower cycloalkyl group, an aryl group, a heterocyclic group, a loweralkoxycarbonyl group or an aryloxycarbonyl group; and/or

(a8) Y represents a lower alkylene group; and/or

(a9) Z represents a chalcogen atom; and/or

(a10) p represents 0, 1, 2 or 3, in the case where p is 2 or 3, each R⁶may be the same or different.

That is, in the compounds represented by the general formula (1) andsalts thereof, preferred examples include compounds that comprise one ora combination of two or more selected from the above (a1), (a2), (a3),(a4), (a5), (a6), (a7), (a8), (a9) and (a10), and salts thereof.

(b) More preferred examples of the present compound include compounds inwhich the respective groups are groups as defined below and saltsthereof in the compounds represented by the general formula (1) andsalts thereof.

(b1) R¹ represents a hydrogen atom or a lower alkyl group; and/or

(b2) R² represents a hydrogen atom or a lower alkyl group; and/or

(b3) R³ and R⁴ may be the same or different and represent a hydrogenatom or a lower alkyl group; and/or

(b4) R⁵ represents a hydrogen atom or a lower alkyl group; and/or

(b5) R⁶ represents a halogen atom, a lower alkyl group, a hydroxy group,a lower alkoxy group or a nitro group; and/or

(b6) X represents —CO—, —C(O)NR⁸—, —S(O)— or —S(O)₂—; and/or

(b7) R⁷ and/or R⁸ may be the same or different and represent a hydrogenatom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group,a lower cycloalkyl group, an aryl group, a heterocyclic group, a loweralkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, alower cycloalkyloxy group, an aryloxy group or a heterocyclic oxy group;

in the case where R⁷ and/or R⁸ is a lower alkyl group, a lower alkenylgroup, a lower alkynyl group, a lower alkoxy group, a lower alkenyloxygroup or a lower alkynyloxy group, the lower alkyl group, lower alkenylgroup, lower alkynyl group, lower alkoxy group, lower alkenyloxy groupor lower alkynyloxy group may have one or a plurality of groups selectedfrom a halogen atom, a lower cycloalkyl group, an aryl group, aheterocyclic group, a hydroxy group, a lower alkoxy group, a lowercycloalkyloxy group, an aryloxy group, a heterocyclic oxy group and—NR^(a)R^(b) as substituent(s);

in the case where R⁷ and/or R⁸ is a lower cycloalkyl group, an arylgroup, a heterocyclic group, a lower cycloalkyloxy group, an aryloxygroup or a heterocyclic oxy group, the lower cycloalkyl group, arylgroup, heterocyclic group, lower cycloalkyloxy group, aryloxy group orheterocyclic oxy group may have one or a plurality of groups selectedfrom a halogen atom, a lower alkyl group, a halogenated lower alkylgroup, a lower cycloalkyl group, an aryl group, a hydroxy group, a loweralkoxy group, a halogenated lower alkoxy group, a cycloalkyloxy group,an aryloxy group, a mercapto group, a lower alkylthio group, a lowercycloalkylthio group, an arylthio group, a heterocyclic thio group, alower alkylcarbonyl group, an arylcarbonyl group, a lower alkoxycarbonylgroup, an aryloxycarbonyl group, a lower alkylcarbonyloxy group, anarylcarbonyloxy group, —NR^(a)R^(b), a nitro group and a cyano group assubstituent(s);

R^(a) and R^(b) may be the same or different and represent a hydrogenatom, a lower alkyl group or a lower alkoxycarbonyl group; and/or

(b8) Y represents a lower alkylene group; and/or

(b9) Z represents an oxygen atom or a sulfur atom; and/or

(b10) p represents 0, 1, 2 or 3, in the case where p is 2 or 3, each R⁶may be the same or different.

That is, in the compounds represented by the general formula (1) andsalts thereof, more preferred examples include compounds that compriseone or a combination of two or more selected from the above (b1), (b2),(b3), (b4), (b5), (b6), (b7), (b8), (b9) and (b10), and salts thereof.

(c) Further more preferred examples of the present compound includecompounds in which the respective groups are groups as defined below andsalts thereof in the compounds represented by the general formula (1)and salts thereof.

(c1) R¹ represents a lower alkyl group; and/or

(c2) R² represents a hydrogen atom; and/or

(c3) R³ and R⁴ represent a lower alkyl group; and/or

(c4) R⁵ represents a lower alkyl group; and/or

(c5) R⁶ represents a halogen atom, a lower alkyl group, a hydroxy group,a lower alkoxy group or a nitro group; and/or

(c6) X represents —CO—, —C(O)NR⁸— or —S(O)₂—; and/or

(c7) R⁷ represents a lower alkyl group, a lower alkenyl group, a lowercycloalkyl group, an aryl group, a heterocyclic group, a lower alkoxygroup or an aryloxy group;

in the case where R⁷ is a lower alkyl group or a lower alkoxy group, thelower alkyl group or lower alkoxy group may have one or a plurality ofgroups selected from a halogen atom, an aryl group, a heterocyclicgroup, a lower alkoxy group and —NR^(a)R^(b) as substituent(s);

in the case where R⁷ is an aryl group, a heterocyclic group or anaryloxy group, the aryl group, heterocyclic group or aryloxy group mayhave one or a plurality of groups selected from a halogen atom, a loweralkyl group, a halogenated lower alkyl group, an aryl group, a hydroxygroup, a lower alkoxy group, a halogenated lower alkoxy group, a loweralkylthio group, a lower alkylcarbonyl group, a lower alkoxycarbonylgroup, a lower alkylcarbonyloxy group, —NR^(a)R^(b), a nitro group and acyano group as substituent(s);

R^(a) and R^(b) may be the same or different and represent a hydrogenatom, a lower alkyl group or a lower alkoxycarbonyl group; and/or

(c8) R⁸ represents a hydrogen atom or a lower alkyl group;

in the case where R⁸ is a lower alkyl group, the lower alkyl group mayhave one or a plurality of groups selected from an aryl group or aheterocyclic group as substituent(s); and/or

(c9) Y represents a lower alkylene group; and/or

(c10) Z represents an oxygen atom; and/or

(c11) p represents 0, 1 or 2, in the case where p is 2, each R⁶ may bethe same or different.

That is, in the compounds represented by the general formula (1) andsalts thereof, further more preferred examples include compounds thatcomprise one or a combination of two or more selected from the above(c1), (c2), (c3), (c4), (c5), (c6), (c7), (c8), (c9), (c10) and (c11),and salts thereof.

(d) Further more preferred examples of the present compound includecompounds in which the respective groups are groups as defined below andsalts thereof in the compounds represented by the general formula (1)and salts thereof.

(d1) R¹ represents a lower alkyl group; and/or

(d2) R² represents a hydrogen atom; and/or

(d3) R³ and R⁴ represent a lower alkyl group; and/or

(d4) R⁵ represents a lower alkyl group; and/or

(d5) R⁶ represents a halogen atom, a lower alkyl group, a hydroxy group,a lower alkoxy group or a nitro group; and/or

(d6) X represents —CO—, —C(O)NR⁸— or —S(O)₂—; and/or

(d7) R⁷ represents a lower alkyl group, a lower alkenyl group, a lowercycloalkyl group, an aryl group, a heterocyclic group, a lower alkoxygroup or an aryloxy group;

in the case where R⁷ is a lower alkyl group, the lower alkyl group mayhave one or a plurality of groups selected from a halogen atom, an arylgroup, a heterocyclic group, a lower alkoxy group and —NR^(a)R^(b) assubstituent(s);

in the case where R⁷ is an aryl group, the aryl group may have one or aplurality of groups selected from a halogen atom, a lower alkyl group, ahalogenated lower alkyl group, a lower alkoxy group, a halogenated loweralkoxy group, a lower alkylthio group, a lower alkylcarbonyl group, alower alkoxycarbonyl group, a lower alkylcarbonyloxy group,—NR^(a)R^(b), a nitro group and a cyano group as substituent(s);

in the case where R⁷ is a heterocyclic group, the heterocyclic group mayhave one or a plurality of groups selected from a halogen atom, a loweralkyl group, an aryl group, a hydroxy group, a lower alkoxy group, alower alkylthio group, a lower alkylcarbonyl group, a loweralkoxycarbonyl group or a nitro group as substituent(s);

in the case where R⁷ is a lower alkoxy group, the lower alkoxy group mayhave one or a plurality of aryl group as substituent(s);

in the case where R⁷ is an aryloxy group, the aryloxy group may have oneor a plurality of groups selected from a halogen atom and a lower alkoxygroup as substituent(s);

R^(a) and R^(b) may be the same or different and represent a hydrogenatom, a lower alkyl group or a lower alkoxycarbonyl group; and/or

(d8) R⁸ represents a hydrogen atom or a lower alkyl group;

in the case where R⁸ is a lower alkyl group, the lower alkyl group mayhave one or a plurality of groups selected from an aryl group or aheterocyclic group as substituent(s); and/or

(d9) Y represents a lower alkylene group; and/or

(d10) Z represents an oxygen atom; and/or

(d11) p represents 0, 1 or 2, in the case where p is 2, each R⁶ may bethe same or different.

That is, in the compounds represented by the general formula (1) andsalts thereof, further more preferred examples include compounds thatcomprise one or a combination of two or more selected from the above(d1), (d2), (d3), (d4), (d5), (d6), (d7), (d8), (d9), (d10) and (d11),and salts thereof.

(e) Specific examples of the present compound represented by thepreferred substituent(s) include compounds in which Z represents anoxygen atom in the general formula (1) and satisfy the above conditions(a) and/or (b), and salts thereof.

(f) Other specific examples of the present compound represented by thepreferred substituent(s) include compounds in which R¹, R³, R⁴ and R⁵represent a methyl group, R² represents a hydrogen atom, Y represents amethylene group in the general formula (1) and satisfy the aboveconditions (a), (b), (c) and/or (d), and salts thereof.

(g) Particularly preferred specific examples of the present compoundinclude the following compounds and salts thereof.

-   6-(4-Benzoyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-(4-t-Butoxycarbonylaminoacetoxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-methoxybenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3-methoxybenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-methoxybenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[4-(2-Chlorobenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-(4-Cyclohexylcarbonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(pyridin-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-(4-Butyryloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-(2-methoxy-4-propionyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-(4-Acryloyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(thiophen-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[4-(furan-2-ylcarbonyloxy)-2-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-(4-isobutyryloxy-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-(2-methoxy-4-phenylacetoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-(2-methoxy-5-propionyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(thiophen-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3-phenylpropionyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[4-(furan-3-ylcarbonyloxy)-2-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(pyridin-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-nitrobenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(pyridin-4-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-5-(pyridin-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-5-(pyridin-4-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[4-(2-Acetoxybenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[4-(1-t-Butoxycarbonylpiperidin-4-ylcarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-methylthiobenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[4-(1-t-Butoxycarbonylimidazol-4-ylcarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(thiazol-4-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(thiazol-5-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(oxazol-4-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[4-(3-Acetylbenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[4-(2-Fluorobenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[4-(3-Fluorobenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(5-methylfuran-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-methylpyridin-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(pyridin-3-ylacetoxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[4-(4-Acetylbenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3-methoxycarbonylbenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(6-methylpyridin-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-methylpyridin-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3-methylfuran-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-(4-t-Butylcarbonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(pyrimidin-5-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(5-nitrofuran-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[4-(2-Chloropyridin-4-ylcarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[4-(3-fluoropyridin-4-ylcarbonyloxy)-2-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[2-Methoxy-4-(2-methoxybenzoyloxy)phenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[2-Methoxy-4-(pyridin-3-ylcarbonyloxy)phenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[4-(Furan-2-ylcarbonyloxy)-2-methoxyphenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[4-(2-Chlorobenzoyloxy)-2-methoxyphenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[2-Methoxy-4-(2-methylpyridin-3-ylcarbonyloxy)phenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[2-Methoxy-4-(2-methoxybenzoyloxy)phenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(2-Methoxy-5-nitrophenoxymethyl)-6-[2-methoxy-4-(thiophen-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[4-(Furan-3-ylcarbonyloxy)-2-methoxyphenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[2-Methoxy-4-(2-methylpyridin-3-ylcarbonyloxy)phenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-methoxypyridin-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-(4-Aminoacetoxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-(2-methoxy-4-propylsulfonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-(4-Ethylsulfonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-(4-isopropylsulfonyl    oxy-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-(4-Butylsulfonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(2-Methoxy-5-nitrophenoxymethyl)-6-(2-methoxy-4-propylsulfonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-(4-Cyclopropylsulfonyloxy-2-methoxyphenyl)-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-(4-Isopropylsulfonyloxy-2-methoxyphenyl)-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-(4-Ethylsulfonyloxy-2-methoxyphenyl)-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-(2-Methoxy-4-propylsulfonyloxyphenyl)-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-(4-Isopropylsulfonyloxy-2-methoxyphenyl)-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-(4-Cyclopropylsulfonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-(4-isobutylsulfonyloxy-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-(4-Cyclopentylsulfonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3,3,3-trifluoropropylsulfonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-methoxyphenoxycarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[4-(2-Chlorophenylaminocarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3-methoxyphenylaminocarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-methoxyphenylaminocarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-methoxycarbonylphenylaminocarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-(4-Dimethylaminocarbonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[4-(4-Cyanophenylaminocarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(morpholin-4-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-(4-Isopropylaminocarbonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[2-Methoxy-4-(morpholin-4-ylcarbonyloxy)phenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[2-Methoxy-4-(morpholin-4-ylcarbonyloxy)phenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-(4-Dimethylaminocarbonyloxy-2-methoxyphenyl)-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[4-[N-Benzyl-N-(2-dimethylaminoethyl)aminocarbonyloxy]-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[4-[N-(2-Dimethylaminoethyl)-N-(pyridin-3-ylmethyl)aminocarbonyloxy]-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,-   6-[4-[N-(2-Dimethylaminoethyl)-N-ethylaminocarbonyloxy]-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline.

The present compound can be synthesized according to the followingprocedures. The individual concrete preparation procedures are explainedin details in the section of “Production Examples” in Examples. Theseexamples are intended to make the present invention more clearlyunderstandable, and do not limit the scope of the present invention. Thehal shown in the following synthetic routes represents a halogen atom.

The present compound (I)-(a) (the compound in which Y is a methylenegroup, R² is H, R³, R⁴ and R⁵ are methyl groups, X is C(O) in thegeneral formula (1)) can be synthesized according to the syntheticroute 1. Namely, the compound (I)-(a) can be given by the reaction ofthe compound (II) with a corresponding halide (III) in an organicsolvent such as methylene dichloride, N,N-dimethylformamide (hereinafterreferred to as DMF) in the presence of a base such as triethylamine,diisopropylethylamine (hereinafter referred to as DIEA) at 0° C. to roomtemperature for 1 hour to 2 days.

And the compound (I)-(a) can be given by the reaction of the compound(II) with a corresponding carboxylic acid (IV) in an organic solventsuch as methylene dichloride, DMF in the presence of a base such astriethylamine, DIEA and a condensation agent such asN,N′-dicyclohexylcarbodiimide,O-(7-azabenzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate at 0° C. to room temperature for 30 minutes to 3days.

The present compound (I)-(b) (the compound in which Y is a methylenegroup, R² is H, R³, R⁴ and R⁵ are methyl groups, X is S(O)₂ in thegeneral formula (1)) can be synthesized according to the synthetic route2. Namely, the compound (I)-(b) can be given by the reaction of thecompound (II) with a corresponding halide (V) in an organic solvent suchas methylene dichloride, DMF in the presence of a base such astriethylamine, DIEA at 0° C. to room temperature for 1 hour to 2 days.

The present compound (I)-(c) (the compound in which Y is a methylenegroup, R² is H, R³, R⁴ and R⁵ are methyl groups, X is C(O)NR⁸ and R⁸ isa hydrogen atom in the general formula (1)) can be synthesized accordingto the synthetic route 3. Namely, the compound (I)-(c) can be given bythe reaction of the compound (II) with a corresponding isocyanate (VI)in an organic solvent such as methylene dichloride, DMF in the presenceof a base such as triethylamine, DIEA at 0° C. to room temperature for30 minutes to 1 day.

The present compound (I)-(d) (the compound in which Y is a methylenegroup, R² is H, R³, R⁴ and R⁵ are methyl groups, X is C(O)NR⁸ in thegeneral formula (1)) can be synthesized according to the synthetic route4. Namely, the compound (I)-(d) can be given by the reaction of thecompound (II) with 1,1′-carbonyldiimidazole in an organic solvent suchas methylene dichloride, tetrahydrofuran (hereinafter referred to asTHF) at room temperature to 50° C. for 30 minutes to 12 hours followedby the reaction with a corresponding amine (VII) at room temperature to50° C. for 30 minutes to 5 hours.

The compound (II) can be synthesized according to the synthetic route 5.Namely, the compound (IX) can be given by the reaction of the compound(VIII) with methanesulfonyl chloride in an organic solvent such asmethylene dichloride, DMF in the presence of a base such astriethylamine, DIEA at 0° C. to room temperature for 30 minutes to 3days. The compound (XI) can be given by the reaction of the obtainedcompound (IX) with a corresponding phenol or thiol (X) in an organicsolvent such as DMF, methylene dichloride in the presence of a base suchas potassium carbonate, DIEA, sodium hydride at 50° C. to 100° C. for 1hour to 2 days. The compound (II) can be given by the treatment of theobtained compound (XI) in an organic solvent such as methylenedichloride, 1,4-dioxane in the presence of an acid such as hydrogenchloride, trifluoroacetic acid.

The compound (XI)-(a) (the compound in which Z is an oxygen atom in thecompound (XI)) can be synthesized according to the synthetic route 6.Namely, the compound (XI)-(a) can be given by the reaction of thecompound (VIII) with a corresponding phenol (XII) in an organic solventsuch as benzene, THF in the presence of a phosphine such astriphenylphosphine, tributylphosphine and a reagent such asdiethylazodicarboxylate, diisopropylazodicarboxylate,1,1′-(azodicarbonyl)dipiperidine at room temperature for 1 hour to 2days.

The compound (VIII) can be synthesized according to the synthetic route7. Namely, the compound (XV) can be given by the reaction of a boronicacid (XIII) with a halide or triflate (XIV) in a solvent such as DMF,ethanol, toluene, water in the presence of a base such as cesiumcarbonate, sodium carbonate, potassium phosphate and a catalyst such asbis(triphenylphosphine)palladium (II) dichloride,tetrakis(triphenylphosphine)palladium (0) at 50° C. to 120° C. for 12hours to 2 days. The compound (XVI) can be given by the treatment of theobtained compound (XV) in a solvent such as methylene dichloride, THF inthe presence of an acid such as boron tribromide, hydrogen chloride at−78° C. to room temperature for 1 hour to 1 day. The compound (XVII) canbe given by the treatment of the obtained compound (XVI) under hydrogenatmosphere in an organic solvent such as methanol, ethanol, 1,4-dioxane,THF in the presence of a catalyst such as palladium carbon, platinumdioxide at room temperature for 2 hours to 2 days. The compound (XVIII)can be given by the treatment of the obtained compound (XVII) in acetonein the presence of iodine at 80° C. to 130° C. for 24 hours to 5 days.The compound (XIX) can be given by the reaction of the obtained compound(XVIII) with chlorodimethylether in an organic solvent such as methylenedichloride, DMF in the presence of a base such as potassium carbonate,triethylamine, DIEA. The compound (XX) can be given by the treatment ofthe obtained compound (XIX) in an organic solvent such as diethyl ether,THF and in the presence of a reducing agent such as lithium aluminiumhydride at 0° C. to 50° C. for 1 hour to 1 day. The compound (VIII) canbe given by the reaction of the obtained compound (XX) with acorresponding halide (XXI) in an organic solvent such as DMF, ethanol inthe presence of a base such as potassium carbonate, DIEA at roomtemperature to 100° C. for 1 hour to 24 hours.

A detailed explanation of this matter will be described in the sectionof “Pharmacological Test” in Examples described below. In order to findthe usefulness of the present compound as a pharmaceutical, aglucocorticoid receptor competitor assay was carried out by afluorescence polarization method by using a glucocorticoid receptorcompetitor assay kit (manufactured by Invitrogen, cat No P2816) to studythe glucocorticoid receptor binding activity of the present compound. Asa result, the present compound showed an excellent glucocorticoidreceptor binding activity to the glucocorticoid receptor.

Incidentally, the glucocorticoid receptor is associated with theoccurrence of various diseases as described above, therefore, thepresent compound having an excellent binding activity to theglucocorticoid receptor is useful as a glucocorticoid receptormodulator.

The present compound can be administered either orally or parenterally.Examples of the dosage form include a tablet, a capsule, a granule, apowder, an injection, an eye drop, a suppository, percutaneousabsorption preparation, an ointment, an aerosol (including an inhalant)and the like and such a preparation can be prepared using a commonlyused technique.

For example, an oral preparation such as a tablet, a capsule, a granuleor a powder can be prepared by optionally adding a necessary amount ofan excipient such as lactose, mannitol, starch, crystalline cellulose,light silicic anhydride, calcium carbonate or calcium hydrogenphosphate; a lubricant such as stearic acid, magnesium stearate or talc;a binder such as starch, hydroxypropyl cellulose, hydroxypropylmethylcellulose or polyvinylpyrrolidone; a disintegrant such as carboxymethylcellulose, low-substituted hydroxypropylmethyl cellulose or calciumcitrate; a coating agent such as hydroxypropylmethyl cellulose, macrogolor a silicone resin; a stabilizer such as ethyl p-hydroxybenzoate orbenzyl alcohol; a corrigent such as a sweetener, a sour agent or aflavor, or the like.

A parenteral preparation such as an injection or an eye drop can beprepared by optionally adding a necessary amount of a tonicity agentsuch as sodium chloride, concentrated glycerin, propylene glycol,polyethylene glycol, potassium chloride, sorbitol or mannitol; a buffersuch as sodium phosphate, sodium hydrogen phosphate, sodium acetate,citric acid, glacial acetic acid or trometamol; a surfactant such aspolysorbate 80, polyoxy 40 stearate or polyoxyethylene hydrogenatedcastor oil 60; a stabilizer such as sodium citrate or sodium edetate; apreservative such as benzalkonium chloride, paraben, benzothoniumchloride, p-hydroxybenzoate ester, sodium benzoate or chlorobutanol; apH adjusting agent such as hydrochloric acid, citric acid, phosphoricacid, glacial acetic acid, sodium hydroxide, sodium carbonate or sodiumhydrogen carbonate; a soothing agent such as benzyl alcohol, or thelike.

This invention also provides a preventive or therapeutic method forglucocorticoid receptor related diseases, for examples, metabolicdisorders such as diabetes and obesity, inflammatory diseases such asenteritis and chronic obstructive pulmonary diseases, autoimmunediseases such as connective tissue diseases, allergic diseases such asasthma, atopic dermatitis and allergic rhinitis, central nervous systemdiseases such as psychiatric disorders, Alzheimer's disease and drug usedisorders, cardiovascular diseases such as hypertension, hypercalcemia,hyperinsulinemia and hyperlipidemia, homeostasis-related diseasescausing an abnormality of neuro-immune-endocrine balance, glaucoma andthe like.

The dose of the present compound can be appropriately selected dependingon the kinds of the diseases, symptoms, age, dosage form or the like.For example, in the case of an oral preparation, it can be administeredin an amount of generally 0.01 to 1000 mg, preferably 1 to 100 mg perday in a single dose or several divided doses. Further, in the case ofan eye drop, a preparation containing the present compound at aconcentration of generally 0.0001% to 10% (w/v), preferably 0.01% to 5%(w/v) can be administered in a single dose or several divided doses.

Hereinafter, Production Examples of the present compound, PreparationExamples and results of Pharmacological Test will be described. However,these examples are described for the purpose of understanding thepresent invention better and are not meant to limit the scope of thepresent invention.

PRODUCTION EXAMPLES Reference Example 15-Hydroxymethyl-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Reference Compound No. 1-1) Methyl2-(2,4-dimethoxyphenyl)-5-nitrobenzoate (Reference Compound No. 1-1-(1))

A mixture of 2,4-dimethoxyphenylboronic acid (25.0 g, 137 mmol), methyl2-bromo-5-nitrobenzoate (35.7 g, 137 mmol), cesium carbonate (89.4 g,274 mmol) and bis(triphenylphosphine)palladium (II) dichloride (4.81 g,6.85 mmol) was suspended in N,N-dimethylformamide (450 mL), and then thesuspension was stirred under argon atmosphere at 80° C. overnight. Aftercooling down, ethyl acetate (200 mL), diethylether (400 mL) and water(1000 mL) were added thereto and the mixture was separated into a waterphase and an organic layer. The water layer was extracted with a mixedsolvent of ethyl acetate (150 mL)-diethylether (150 mL) (twice). Thecombined organic layer was washed with water (500 mL, 3 times) andsaturated brine (500 mL) successively, dried over anhydrous magnesiumsulfate, and then the solvent was removed under reduced pressure to givethe titled reference compound as a brown oil. (Quantitative)

¹H-NMR (400 MHz, CDCl3) δ 3.71 (s, 3H), 3.76 (s, 3H), 3.87 (s, 3H), 6.49(d, J = 2.3 Hz, 1H), 6.60 (dd, J = 8.3, 2.3 Hz, 1H), 7.20 (d, J = 8.3Hz, 1H), 7.49 (d, J = 8.5 Hz, 1H), 8.35 (dd, J = 8.5, 2.5 Hz, 1H), 8.67(d, J = 2.5 Hz, 1H)

3-Hydroxy-8-nitrobenzo[c]chromen-6-one (Reference Compound No. 1-1-(2))

A solution of methyl 2-(2,4-dimethoxyphenyl)-5-nitrobenzoate (ReferenceCompound No. 1-1-(1), 43.5 g, 137 mmol) in anhydrous methylenedichloride (250 mL) was cooled to −78° C., boron tribromide (96.2 g, 384mmol) was added thereto, and then the mixture was stirred at roomtemperature for 1 hour. The mixture was cooled to −50° C. and methanol(300 mL) was added thereto. The resulting precipitates were filtered offwith methanol to give the titled reference compound (18.0 g) as a yellowsolid. (Yield 51%)

¹H-NMR (400 MHz, DMSO-d₆) δ 6.81 (d, J = 2.4 Hz, 1H), 6.91 (dd, J = 8.8,2.4 Hz, 1H), 8.28 (d, J = 8.8 Hz, 1H), 8.50 (d, J = 8.9 Hz, 1H), 8.60(dd, J = 8.9, 2.4 Hz, 1H), 8.82 (d, J = 2.4 Hz, 1H), 10.75 (s, 1H)

8-Amino-3-hydroxybenzo[c]chromen-6-one (Reference Compound No. 1-1-(3))

3-Hydroxy-8-nitrobenzo[c]chromen-6-one (Reference Compound No. 1-1-(2),52.01 g, 202 mmol) was dissolved in methanol (150mL)-N,N-dimethylformamide (600 mL), 10% palladium on charcoal (5.00 g)was added thereto, and then the reaction mixture was stirred underhydrogen atmosphere (3 kgf/cm²) at room temperature overnight. After theunsoluble materials were filtered out, the methanol was removed underreduced pressure. Water (2 L) was added to the residue. The precipitatedsolid was filtered off and dried at 90° C. under reduced pressure togive the titled reference compound (44.02 g) as a pale yellow solid.(Yield 96%)

¹H-NMR (400 MHz, DMSO-d₆) δ 6.02 (s, 2H), 7.17 (dd, J = 8.5, 2.4 Hz,1H), 7.37-7.41 (m, 1H), 7.37 (d, J = 2.4 Hz, 1H), 7.96 (ddd, J = 9.3,5.4, 2.2 Hz, 1H), 8.08 (d, J = 8.5, Hz, 1H)

8-Hydroxy-2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one(Reference Compound No. 1-1-(4))

In a pressure tube, 8-amino-3-hydroxybenzo[c]chromen-6-one (ReferenceCompound No. 1-1-(3), 40.0 g, 176 mmol) was dissolved in acetone (440mL)-N-methylpyrrolidone (240 mL), iodine (17.9 g, 70.5 mmol) was addedthereto, the pressure tube was sealed, and then the reaction mixture wasstirred at 110° C. for 3 days. After cooling down, acetone was removedunder reduced pressure. To the obtained residue, ethyl acetate (700 mL),hexane (150 mL) and 1% aqueous sodium thiosulfate solution (700 mL) wereadded thereto and the mixture was separated into a water phase and anorganic layer. The water layer was extracted with a mixed solvent ofethyl acetate (250 mL)-hexane (50 mL) (3 times). The combined organiclayer was washed with water (500 mL, 3 times) and saturated brine (500mL) successively, dried over anhydrous magnesium sulfate, and then thesolvent was removed under reduced pressure. To the obtained residue,chloroform (150 mL) was added and the unsoluble materials were filteredout. After the filtrate was concentrated, the residue was purified bysilica gel column chromatography (hexane-ethyl acetate) to give thetitled reference compound (26.0 g) as a yellow solid. (Yield 48%)

¹H-NMR (500 MHz, DMSO-d₆) δ 1.23 (s, 6H), 1.97 (s, 3H), 5.48 (s, 1H),7.05 (s, 1H), 7.19 (d, J = 8.9 Hz, 1H), 7.37 (td, J = 9.7, 7.6 Hz, 1H),7.95 (ddd, J = 9.7, 5.2, 1.8 Hz, 1H), 7.98 (d, J = 8.9, Hz, 1H)

8-Methoxymethoxy-2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one(Reference Compound No. 1-1-(5))

A mixture of8-hydroxy-2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one(Reference Compound No. 1-1-(4), 1.00 g, 3.25 mmol), chlorodimethylether(420 μL, 5.53 mmol) and potassium carbonate (1.35 g, 9.77 mmol) wassuspended in anhydrous N,N-dimethylformamide (15 mL) and the suspensionwas stirred at 50° C. overnight. After cooling down, ethyl acetate (100mL) and diethylether (100 mL) were added thereto. The whole was washedwith water (150 mL, 100 mL) and saturated brine (100 mL) successively,dried over anhydrous magnesium sulfate, and then the solvent was removedunder reduced pressure. The obtained residue was purified by silica gelcolumn chromatography (hexane-ethyl acetate) to give the titledreference compound (747 mg) as a yellow solid. (Yield 66%)

¹H-NMR (400 MHz, DMSO-d₆) δ 1.22 (s, 6H), 1.95 (s, 3H), 3.40 (s, 3H),5.27 (s, 2H), 5.43 (s, 1H), 6.85 (s, 1H), 6.98 (d, J = 9.3 Hz, 1H), 6.99(s, 1H), 7.16 (d, J = 8.8 Hz, 1H), 7.92 (d, J = 8.8 Hz, 1H), 8.04 (d, J= 9.3 Hz, 1H)

6-(2-Hydroxy-4-methoxymethoxyphenyl)-5-hydroxymethyl-2,2,4-trimethyl-1,2-dihydroquinoline(Reference Compound No. 1-1-(6))

Lithium aluminum hydride (167 mg, 4.40 mmol) was suspended in anhydroustetrahydrofuran (3 mL). A solution of8-methoxymethoxy-2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one(Reference Compound No. 1-1-(5), 744.1 mg, 2.12 mmol) in anhydroustetrahydrofuran (10 mL) was added dropwise to the suspension at 0° C.,the reaction mixture was stirred at the same temperature for 30 minutes.Ethyl acetate (2 mL) and water (1 mL) were added to the reaction mixturesuccessively, and then ethyl acetate (150 mL) was added thereto. 1Naqueous HCl solution (6 mL) was added, the mixture was washed with water(100 mL, twice) and saturated brine (50 mL) successively, and then driedover anhydrous magnesium sulfate. The solvent was removed under reducedpressure to give the titled reference compound (750.6 mg) as a paleyellow amorphous product. (Quantitative)

¹H-NMR (500 MHz, DMSO-d₆) δ 1.13 (s, 3H), 1.20 (s, 3H), 2.23 (s, 3H),3.39 (s, 3H), 4.26 (dd, J = 11.0, 6.6 Hz, 1H), 4.33 (t, J = 6.6 Hz, 1H),4.44 (dd, J = 11.0, 6.6 Hz, 1H), 5.14 (s, 2H), 5.33 (s, 1H), 5.76 (s,1H), 6.49 (dd, J = 8.4, 2.6 Hz, 1H), 6.53 (d, J = 8.3 Hz, 1H), 6.56 (d,J = 2.6 Hz, 1H), 6.65 (d, J = 8.3 Hz, 1H), 6.97 (d, J = 8.4 Hz, 1H),9.23 (s, 1H)

5-Hydroxymethyl-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Reference Compound No. 1-1)

A mixture of6-(2-hydroxy-4-methoxymethoxyphenyl)-5-hydroxymethyl-2,2,4-trimethyl-1,2-dihydroquinoline(Reference Compound No. 1-1-(6), 746.1 mg, 2.10 mmol), methyl iodide(131 μL, 2.10 mmol) and potassium carbonate (582 mg, 4.21 mmol) wassuspended in anhydrous N,N-dimethylformamide (10 mL) and the suspensionwas stirred at 50° C. for 1 hour. After cooling down, the mixture wasdiluted with ethyl acetate (50 mL) and diethylether (50 mL). The mixturewas washed with water (100 mL, twice) and saturated brine (50 mL)successively, dried over anhydrous magnesium sulfate, and then thesolvent was removed under reduced pressure. The obtained residue waspurified by silica gel column chromatography (hexane-ethyl acetate) togive the titled reference compound (513.2 mg) as a colorless solid.(Yield 66%)

¹H-NMR (400 MHz, DMSO-d₆) δ 1.13 (s, 3H), 1.20 (s, 3H), 2.23 (s, 3H),3.41 (s, 3H), 3.65 (s, 3H), 4.14 (d, J = 12.2 Hz, 1H), 4.33 (br s, 1H),4.45 (d, J = 12.2 Hz, 1H), 5.22 (s, 2H), 5.32 (s, 1H), 5.78 (s, 1H),6.51 (d, J = 8.3 Hz, 1H), 6.61-6.64 (m, 2H), 6.66 (d, J = 2.4 Hz, 1H),7.05 (d, J = 8.3 Hz, 1H)Using available compounds, the following Reference Compound No. 1-2 wasobtained by a method similar to that of Reference Compound No. 1-1.

5-Hydroxymethyl-6-(2-methoxy-5- methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 1-2)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.13 (s, 3H), 1.21 (s, 3H), 2.24 (s, 3H),3.38 (s, 3H), 3.62 (s, 3H), 4.15 (dd, J = 12.2, 4.7 Hz, 1H), 4.38 (t, J= 4.7 Hz, 1H), 4.47 (dd, J = 12.2, 4.7 Hz, 1H), 5.11 (d, J = 6.5 Hz,1H), 5.13 (d, J = 6.5 Hz, 1H), 5.33 (s, 1H), 5.84 (s, 1H), 6.53 (d, J =8.2 Hz, 1H), 6.66 (d, J = 8.2 Hz, 1H), 6.85 (d, J = 2.6 Hz,1H),6.90-6.96 (m, 2H)

Reference Example 25-(5-Fluoro-2-methylphenoxymethyl)-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Reference Compound No. 2-1)

5-Hydroxymethyl-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Reference Compound No. 1-1, 511.7 mg, 1.39 mmol),5-fluoro-2-methylphenol (182 μL, 1.67 mmol), tri-n-butylphosphine (521μL, 2.09 mmol), and 1,1′-(azodicarbonyl)dipiperidine (526 mg, 2.08 mmol)were dissolved in anhydrous benzene (8 mL), and then the mixture wasstirred under argon atmosphere at room temperature for 1 hour. Hexane(15 mL) was added to the reaction mixture, and the unsoluble materialswere filtered out. The filtrate was concentrated under reduced pressureand the residue was purified by silica gel column chromatography(hexane-ethyl acetate) to give the titled reference compound (411.4 mg)as a colorless amorphous product. (Yield 62%)

¹H-NMR (400 MHz, DMSO-d₆) δ 1.13 (s, 3H), 1.20 (s, 3H), 2.23 (s, 3H),3.41 (s, 3H), 3.65 (s, 3H), 4.14 (d, J = 12.2 Hz, 1H), 4.33 (br s, 1H),4.45 (d, J = 12.2 Hz, 1H), 5.22 (s, 2H), 5.32 (s, 1H), 5.78 (s, 1H),6.51 (d, J = 8.3 Hz, 1H), 6.61- 6.64 (m, 2H), 6.66 (d, J = 2.4 Hz, 1H),7.05 (d, J = 8.3 Hz, 1H)Using Reference Compound No. 1-1 or 1-2, the following ReferenceCompounds (No. 2-2˜2-4) were obtained by a method similar to that ofReference Compound No. 2-1.

5-(5-Fluoro-2-methylphenoxymethyl)-6-(2-methoxy-5-methoxymethoxyphenyl)- 2,2,4-trimethyl-1,2-dihydroquinoline(Reference Compound No. 2-2)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.15 (s, 3H), 2.02 (s, 3H),2.08 (s, 3H), 3.29 (s, 3H), 3.67 (s, 3H), 4.62 (d, J = 12.1 Hz, 1H),5.02 (d, J = 6.7 Hz, 1H), 5.06 (d, J = 6.7 Hz, 1H), 5.10 (d, J = 12.1Hz, 1H), 5.39 (s, 1H), 6.02 (s, 1H), 6.35 (dd, J = 11.6, 2.4 Hz, 1H),6.52 (td, J = 8.4, 2.4 Hz, 1H), 6.63 (d, J = 8.2 Hz, 1H), 6.79 (d, J =8.2 Hz, 1H), 6.86 (d, J = 2.7 Hz, 1H), 6.95 (dd, J = 8.9, 2.7 Hz, 1H),6.97 (d, J = 8.9 Hz, 1H), 7.02- 7.05 (m, 1H)6-(2-Methoxy-4-methoxymethoxyphenyl)-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4- trimethyl-1,2-dihydroquinoline(Reference Compound No. 2-3)  

¹H-NMR (400 MHz, DMSO-d₆) δ 0.87 (s, 3H), 1.17 (s, 3H), 2.13 (s, 3H),2.18 (s, 3H), 3.39 (s, 3H), 3.72 (s, 3H), 4.79 (d, J = 12.7 Hz, 1H),5.21 (s, 2H), 5.31 (d, J = 12.7 Hz, 1H), 5.38 (s, 1H), 5.97 (s, 1H),6.59 (d, J = 8.2 Hz, 1H), 6.65 (dd, J = 8.2, 2.4 Hz, 1H), 6.70 (d, J =2.4 Hz, 1H), 6.76 (d, J = 8.2 Hz, 1H), 7.12 (d, J = 2.1 Hz, 1H), 7.17(d, J = 8.2 Hz, 1H), 7.32 (d, J = 8.7 Hz, 1H), 7.62 (dd, J = 8.7, 2.1Hz, 1H) 6-(2-Methoxy-4-methoxymethoxyphenyl)-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline (ReferenceCompound No. 2-4)  

1H-NMR (400 MHz, DMSO-d₆) δ 1.01 (s, 3H), 1.17 (s, 3H), 2.14 (s, 3H),3.67 (s, 3H), 3.82 (s, 3H), 3.90 (s, 3H), 4.67 (d, J = 12.1 Hz, 1H),5.17 (s, 2H), 5.25 (d, J = 12.1 Hz, 1H), 5.38 (s, 1H), 5.96 (s, 1H),6.54 (dd, J = 8.4, 2.3 Hz, 1H), 6.59 (d, J = 8.1 Hz, 1H), 6.64 (d, J =2.3 Hz, 1H), 6.72 (d, J = 8.1 Hz, 1H), 7.04 (d, J = 8.4 Hz, 1H), 7.08(d, J = 8.9 Hz, 1H), 7.28 (d, J = 2.7 Hz, 1H), 7.80 (dd, J = 8.9, 2.7Hz, 1H)

Reference Example 35-(5-Fluoro-2-methylphenoxymethyl)-6-(4-hydroxy-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Reference Compound No. 3-1)

5-(5-Fluoro-2-methylphenoxymethyl)-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Reference Compound No. 2-1, 424 mg, 0.888 mmol) was dissolved in1,4-dioxane (5 mL), 4N HCl/1,4-dioxane solution (666 μL) was addedthereto, and then the mixture was stirred at room temperature overnight.The mixture was diluted with ethyl acetate (150 mL). The mixture waswashed with water (100 mL, twice) and saturated brine (50 mL)successively, dried over anhydrous magnesium sulfate, and then thesolvent was removed under reduced pressure. The obtained residue waspurified by silica gel column chromatography (hexane-ethyl acetate) togive the titled reference compound (241.7 mg) as a colorless solid.(Yield 63%)

¹H-NMR (400 MHz, DMSO-d₆) δ 1.00 (s, 3H), 1.14 (s, 3H), 2.01 (s, 3H),2.08 (s, 3H), 3.67 (s, 3H), 4.63 (d, J = 12.1 Hz, 1H), 5.08 (d, J = 12.1Hz, 1H), 5.37 (s, 1H), 5.90 (s, 1H), 6.29 (dd, J = 11.5, 2.4 Hz, 1H),6.36 (dd, J = 8.1, 2.3 Hz, 1H), 6.45 (d, J = 2.3 Hz, 1H), 6.50 (td, J =8.4, 2.4 Hz, 1H), 6.58 (d, J = 8.1 Hz, 1H), 6.73 (d, J = 8.1 Hz, 1H),6.94 (d, J = 8.1 Hz, 1H), 7.00- 7.04 (m, 1H), 9.46 (s, 1H)Using any compounds among Reference Compounds No. 2-2˜2-4, the followingReference Compounds (No. 3-2˜3-4) were obtained by a method similar tothat of Reference Compound No. 3-1.

5-(5-Fluoro-2-methylphenoxymethyl)-6- (5-hydroxy-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 3-2)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.02 (s, 3H), 1.15 (s, 3H), 2.01 (s, 3H),2.06 (s, 3H), 3.61 (s, 3H), 4.65 (d, J = 12.2 Hz, 1H), 5.10 (d, J = 12.2Hz, 1H), 5.38 (s, 1H), 5.99 (s, 1H), 6.33 (dd, J = 11.5, 2.4 Hz, 1H),6.51 (td, J = 8.4, 2.4 Hz, 1H), 6.59 (d, J = 2.9 Hz, 1H), 6.61 (d, J =8.3 Hz, 1H), 6.67 (dd, J = 8.8, 2.9 Hz, 1H), 6.75 (d, J = 8.3 Hz, 1H),6.85 (d, J = 8.8 Hz, 1H), 7.00-7.04 (m, 1H), 8.93 (s, 1H)6-(4-Hydroxy-2-methoxyphenyl)-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl- 1,2-dihydroquinoline(Reference Compound No. 3-3)  

¹H-NMR (400 MHz, DMSO-d₆) δ 0.85 (s, 3H), 1.17 (s, 3H), 2.13 (s, 3H),2.18 (s, 3H), 3.68 (s, 3H), 4.79 (d, J = 12.5 Hz, 1H), 5.30 (d, J =12.5Hz, 1H), 5.37 (s, 1H), 5.92 (s, 1H), 6.40 (dd, J = 8.2, 2.3 Hz, 1H),6.46 (d, J = 2.3 Hz, 1H), 6.57 (d, J = 8.3 Hz, 1H), 6.74 (d, J = 8.3 Hz,1H), 7.05 (d, J = 8.2 Hz, 1H), 7.11 (d, J = 2.3 Hz, 1H), 7.32 (d, J =8.3 Hz, 1H), 7.62 (dd, J = 8.3, 2.3 Hz, 1H), 9.50 (s, 1H)(6-(4-Hydroxy-2-methoxyphenyl)-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-di- hydroquinoline (ReferenceCompound No.3-4)

¹H-NMR (400 MHz, DMSO-d₆) δ 0.98 (s, 3H), 1.17 (s, 3H), 2.13 (s, 3H),3.63 (s, 3H), 3.82 (s, 3H), 4.67 (d, J = 12.0 Hz, 1H), 5.24 (d, J = 12.0Hz, 1H), 5.36 (s, 1H), 5.90 (s, 1H), 6.28 (dd, J = 8.3, 2.2 Hz, 1H),6.40 (d, J = 2.2 Hz, 1H), 6.58 (d, J = 8.2 Hz, 1H), 6.71 (d, J = 8.2 Hz,1H), 6.94 (d, J = 8.3 Hz, 1H), 7.08 (d, J = 9.2 Hz, 1H), 7.28 (d, J =2.8 Hz, 1H), 7.79 (dd, J = 9.2, 2.8 Hz, 1H), 9.40 (s, 1H)

Example 16-(4-Benzoyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 1-1)

5-(5-Fluoro-2-methylphenoxymethyl)-6-(4-hydroxy-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Reference Compound No. 3-1, 25.5 mg, 0.588 mmol) was dissolved inanhydrous tetrahydrofuran (0.5 mL), then triethylamine (19.7 μL, 0.141mmol) and benzoyl chloride (8.2 μL, 0.071 mmol) were added thereto. Thereaction mixture was stirred at room temperature for 30 minutes. Themixture was diluted with ethyl acetate (100 mL). The mixture was washedwith water (100 mL) and saturated brine (50 mL) successively, dried overanhydrous magnesium sulfate, and then the solvent was removed underreduced pressure. The obtained residue was purified by silica gel columnchromatography (hexane-ethyl acetate) to give the titled compound (26.7mg) as a colorless solid. (Yield 63%)

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.65 (d, J = 12.1 Hz, 1H), 5.10 (d, J = 12.1Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.38 (dd, J = 11.5, 2.4 Hz, 1H),6.54 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.2 Hz, 1H), 6.82 (d, J =8.2 Hz, 1H), 6.89 (dd, J = 8.2, 2.3 Hz, 1H), 7.03-7.06 (m, 1H), 7.05 (d,J = 2.3 Hz, 1H), 7.24 (d, J = 8.2 Hz, 1H), 7.62 (t, J = 7.4 Hz, 2H),7.76 (t, J = 7.4 Hz, 1H), 8.15 (d, J = 7.4 Hz, 2H)

6-(4-t-Butoxycarbonylaminoacetoxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 1-2)

5-(5-Fluoro-2-methylphenoxymethyl)-6-(4-hydroxy-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Reference Compound No. 3-1, 30.2 mg, 0.070 mmol) and Boc-glycine (15.1mg, 0.086 mmol) were dissolved in N,N-dimethylformamide (1 mL),N,N-diisopropylethylamine (31.4 μL, 0.18 mmol) andO-(7-azabenzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate (35.4 mg, 0.093 mmol) were added thereto, and thenthe mixture was stirred at room temperature overnight. Ethyl acetate (10mL) was added to the reaction mixture, then the mixture was washed withwater (10 mL) and saturated brine (10 mL) successively. The organiclayer was dried over anhydrous magnesium sulfate and the solvent wasremoved under reduced pressure. The obtained residue was purified bysilica gel column chromatography (hexane-ethyl acetate) to give thetitled compound (35.3 mg) as a colorless amorphous product. (Yield 86%)

¹H-NMR (400 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.15 (s, 3H), 1.40 (s, 9H),2.01 (s, 3H), 2.07 (s, 3H), 3.71 (s, 3H), 3.96 (d, J = 6.0 Hz, 2H), 4.61(d, J = 12.1 Hz, 1H), 5.07 (d, J = 12.1 Hz, 1H), 5.39 (s, 1H), 6.04 (s,1H), 6.34 (d, J = 11.5 Hz, 1H), 6.52 (td, J = 8.4, 2.4 Hz, 1H), 6.63 (d,J = 8.2 Hz, 1H), 6.71 (dd, J = 8.3, 2.3 Hz, 1H), 6.78 (d, J = 8.2 Hz,1H), 6.83 (d, J = 2.3 Hz, 1H), 7.01-7.05 (m, 1H), 7.19 (d, J = 8.3 Hz,1H), 7.40 (t, J = 6.0 Hz, 1H)Using any compounds among Reference Compounds No. 3-1˜3-4, the followingCompounds (No. 1-3˜1-125) were obtained by a method similar to that ofCompound No. 1-1 or 1-2.

5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-methylbenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-3)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 2.43 (s, 3H), 3.74 (s, 3H), 4.65 (d, J = 12.1 Hz, 1H),5.10 (d, J = 12.1 Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.37 (dd, J =11.5, 2.4 Hz, 1H), 6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.2 Hz,1H), 6.81 (d, J = 8.2 Hz, 1H), 6.87 (dd, J = 8.2, 2.3 Hz, 1H), 7.02-7.06(m, 1H), 7.03 (d, J = 2.3 Hz, 1H), 7.23 (d, J = 8.2 Hz, 1H), 7.42 (d, J= 8.2 Hz, 2H), 8.04 (d, J = 8.2 Hz, 2H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3-methylbenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-4)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 2.42 (s, 3H), 3.74 (s, 3H), 4.65 (d, J = 12.1 Hz, 1H),5.10 (d, J = 12.1 Hz, 1H), 5.40 (s, 1H), 6.03 (s, 1H), 6.38 (dd, J =11.3, 2.4 Hz, 1H), 6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.1 Hz,1H), 6.81 (d, J = 8.1 Hz, 1H), 6.88 (dd, J = 8.2, 2.2 Hz, 1H), 7.03-7.06(m, 1H), 7.03 (d, J = 2.2 Hz, 1H), 7.23 (d, J = 8.2 Hz, 1H), 7.50 (t, J= 7.8 Hz, 1H), 7.57 (d, J = 7.8 Hz, 1H), 7.94 (d, J = 7.8 Hz, 1H), 7.97(s, 1H) 5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-methylbenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-5)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.15 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 2.61 (s, 3H), 3.75 (s, 3H), 4.66 (d, J = 12.1 Hz, 1H),5.11 (d, J = 12.1 Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.38 (dd, J =11.5, 2.5 Hz, 1H), 6.53 (td, J = 8.4, 2.5 Hz, 1H), 6.65 (d, J = 8.3 Hz,1H), 6.81 (d, J = 8.3 Hz, 1H), 6.89 (dd, J = 8.2, 2.2 Hz, 1H), 7.02-7.06(m, 1H), 7.05 (d, J = 2.2 Hz, 1H), 7.24 (d, J = 8.2 Hz, 1H), 7.39-7.43(m, 1H), 7.42 (d, J = 7.6 Hz, 1H), 7.56-7.60 (m, 1H), 8.09 (d, J = 8.1Hz, 1H) 5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-methylbenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-6)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 3.88 (s, 3H), 4.65 (d, J = 12.1 Hz, 1H),5.10 (d, J = 12.1 Hz, 1H), 5.40 (s, 1H), 6.03 (s, 1H), 6.37 (dd, J =11.3, 2.4 Hz, 1H), 6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 7.9 Hz,1H), 6.81 (d, J = 7.9 Hz, 1H), 6.86 (dd, J = 8.1, 2.1 Hz, 1H), 7.01 (d,J = 2.1 Hz, 1H), 7.03-7.06 (m, 1H), 7.13 (d, J = 8.9 Hz, 2H), 7.22 (d, J= 8.1 Hz, 1H) 8.10 (d, J = 8.9 Hz, 2H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3-methoxybenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-7)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 3.86 (s, 3H), 4.65 (d, J = 12.0 Hz, 1H),5.10 (d, J = 12.0 Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.38 (dd, J =11.5, 2.5 Hz, 1H), 6.54 (td, J = 8.4, 2.5 Hz, 1H), 6.65 (d, J = 8.1 Hz,1H), 6.81 (d, J = 8.1 Hz, 1H), 6.89 (dd, J = 8.2, 2.2 Hz, 1H), 7.03-7.06(m, 1H), 7.05 (d, J = 2.2 Hz, 1H), 7.24 (d, J = 8.2 Hz, 1H), 7.31-7.34(m, 1H), 7.53 (t, J =7.9 Hz, 1H) 7.62 (dd, J = 2.4, 1.5 Hz, 1H),7.72-7.75 (m, 1H) 5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-methoxybenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-8)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.15 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 3.88 (s, 3H), 4.65 (d, J = 12.1 Hz, 1H),5.10 (d, J = 12.1 Hz, 1H), 5.40 (s, 1H), 6.03 (s, 1H), 6.37 (dd, J =11.4, 2.6 Hz, 1H), 6.53 (td, J = 8.3, 2.4 Hz, 1H), 6.64 (d, J = 8.3 Hz,1H), 6.81 (d, J = 8.3 Hz, 1H), 6.84 (dd, J = 8.3, 2.2 Hz, 1H), 6.98 (d,J = 2.2 Hz, 1H), 7.02- 7.06 (m, 1H), 7.10 (t, J = 7.5 Hz, 1H), 7.23 (d,J = 8.3 Hz, 1H), 7.23 (d, J = 7.5 Hz, 1H), 7.64 (t, J = 7.5 Hz, 1H),7.93 (d, J = 7.5 Hz, 1H)6-[4-(4-Chlorobenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-9)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.65 (d, J = 11.9 Hz, 1H), 5.10 (d, J = 11.9Hz, 1H), 5.40 (s, 1H), 6.03 (s, 1H), 6.37 (dd, J = 11.5, 2.5 Hz, 1H),6.53 (td, J = 8.4, 2.5 Hz, 1H), 6.65 (d, J = 8.1 Hz, 1H), 6.81 (d, J =8.1 Hz, 1H), 6.90 (dd, J = 8.2, 2.4 Hz, 1H), 7.03- 7.07 (m, 1H), 7.06(d, J = 2.4 Hz, 1H), 7.24 (d, J = 8.2 Hz, 1H), 7.69 (d, J = 8.6 Hz, 2H),8.15 (d, J = 8.6 Hz, 2H)6-[4-(3-Chlorobenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-10)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.65 (d, J = 11.9 Hz, 1H), 5.10 (d, J = 11.9Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.38 (dd, J = 11.6, 2.4 Hz, 1H),6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.1 Hz, 1H), 6.81 (d, J =8.1 Hz, 1H), 6.92 (dd, J = 8.2, 2.2 Hz, 1H), 7.03- 7.06 (m, 1H), 7.09(d, J = 2.2 Hz, 1H), 7.24 (d, J = 8.2 Hz, 1H), 7.66 (t, J = 7.9 Hz, 1H),7.84 (ddd, J = 7.9, 2.0, 1.1 Hz, 1H), 8.10 (dt, J = 7.9, 1.1 Hz, 1H),8.12 (t, J = 2.0 Hz, 1H)6-[4-(2-Chlorobenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-11)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.75 (s, 3H), 4.65 (d, J = 12.2 Hz, 1H), 5.10 (d, J = 12.2Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.38 (dd, J = 11.5, 2.4 Hz, 1H),6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.3 Hz, 1H), 6.81 (d, J =8.3 Hz, 1H), 6.91 (dd, J = 8.2, 2.2 Hz, 1H), 7.02- 7.06 (m, 1H), 7.07(d, J = 2.2 Hz, 1H), 7.25 (d, J = 8.2 Hz, 1H), 7.54- 7.58 (m, 1H),7.67-7.69 (m, 2H), 8.10-8.12 (m, 1H)6-(4-Cyclohexylcarbonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo.1-12)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.15 (s, 3H), 1.17-1.72 (m,10H), 1.99-2.01 (m, 1H), 2.01 (s, 3H), 2.07 (s, 3H), 3.71 (s, 3H), 4.61(d, J = 12.1 Hz, 1H), 5.07 (d, J = 12.1 Hz, 1H), 5.39 (s, 1H), 6.03 (s,1H), 6.34 (dd, J = 11.5, 2.4 Hz, 1H), 6.52 (td, J = 8.4, 2.4 Hz, 1H),6.63 (d, J = 8.3 Hz, 1H), 6.70 (dd, J = 8.3, 2.3 Hz, 1H), 6.78 (d, J =8.3 Hz, 1H), 6.82 (d, J = 2.3 Hz, 1H), 7.01-7.05 (m, 1H), 7.17 (d, J =8.3 Hz, 1H) 5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(pyridin-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 1-13)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.65 (d, J = 12.2 Hz, 1H), 5.10 (d, J = 12.2Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.38 (dd, J = 11.4, 2.4 Hz, 1H),6.54 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.3 Hz, 1H), 6.82 (d, J =8.3 Hz, 1H), 6.93 (dd, J = 8.2, 2.2 Hz, 1H), 7.02- 7.06 (m, 1H), 7.11(d, J = 2.2 Hz, 1H), 7.25 (d, J = 8.2 Hz, 1H), 7.66 (ddd, J = 8.0, 4.9,0.8 Hz, 1H), 8.48 (dt, J = 8.0, 2.0 Hz, 1H), 8.91 (dd, J = 4.9, 2.0 Hz,1H), 9.27 (dd, J = 2.0, 0.8 Hz, 1H)6-(4-Butyryloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-14)  

¹H-NMR (400 MHz, DMSO-d₆) δ 0.98 (t, J = 7.3 Hz, 3H), 1.05 (s, 3H), 1.15(s, 3H), 1.64-1.70 (m, 2H), 2.01 (s, 3H), 2.07 (s, 3H), 2.55 (t, J = 7.3Hz, 2H), 3.71 (s, 3H), 4.61 (d, J = 12.2 Hz, 1H), 5.07 (d, J = 12.2 Hz,1H), 5.39 (s, 1H), 6.03 (s, 1H), 6.34 (dd, J = 11.5, 2.4 Hz, 1H), 6.52(td, J = 8.4, 2.4 Hz, 1H), 6.63 (d, J = 8.3 Hz, 1H), 6.71 (dd, J = 8.2,2.2 Hz, 1H), 6.78 (d, J = 8.3 Hz, 1H), 6.84 (d, J = 2.2 Hz, 1H),7.01-7.05 (m, 1H), 7.17 (d, J = 8.2 Hz, 1H)6-(4-Acetoxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-15)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.15 (s, 3H), 2.01 (s, 3H),2.07 (s, 3H), 2.26 (s, 3H), 3.71 (s, 3H), 4.61 (d, J = 12.2 Hz, 1H),5.07 (d, J = 12.2 Hz, 1H), 5.39 (s, 1H), 6.02 (s, 1H), 6.33 (dd, J =11.6, 2.4 Hz, 1H), 6.52 (td, J = 8.4, 2.4 Hz, 1H), 6.63 (d, J = 8.1 Hz,1H), 6.72 (dd, J = 8.2, 2.1 Hz, 1H), 6.78 (d, J = 8.1 Hz, 1H), 6.86 (d,J = 2.1 Hz, 1H), 7.02-7.05 (m, 1H), 7.17 (d, J = 8.2 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-(2-methoxy-4-propionyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-16)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.14 (t, J = 7.5 Hz, 3H), 1.15(s, 3H), 2.01 (s, 3H), 2.07 (s, 3H), 2.59 (q, J = 7.5 Hz, 2H), 3.71 (s,3H), 4.61 (d, J = 12.1 Hz, 1H), 5.07 (d, J = 12.1 Hz, 1H), 5.39 (s, 1H),6.03 (s, 1H), 6.34 (dd, J = 11.5, 2.4 Hz, 1H), 6.52 (td, J = 8.4, 2.4Hz, 1H), 6.63 (d, J = 8.3 Hz, 1H), 6.72 (dd, J = 8.1, 2.2 Hz, 1H), 6.78(d, J = 8.3 Hz, 1H), 6.85 (d, J = 2.2 Hz, 1H), 7.01- 7.05 (m, 1H), 7.17(d, J = 8.1 Hz, 1H) 6-(4-Acryloyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-17)  

¹H-NMR (500 MHz, CDCl₃) δ 1.12 (s, 3H), 1.23 (s, 3H), 2.07 (s, 3H), 2.16(s, 3H), 3.75 (s, 3H), 4.75 (d, J = 11.9 Hz, 1H), 5.11 (d, J = 11.9 Hz,1H), 5.45 (s, 1H), 6.03 (d, J = 10.4 Hz, 1H), 6.19 (dd, J = 11.0, 2.4Hz, 1H), 6.34 (dd, J = 17.7, 10.4 Hz, 1H), 6.42 (td, J = 8.3, 2.4 Hz,1H), 6.58 (d, J = 8.4 Hz, 1H), 6.62 (d, J = 17.7 Hz, 1H), 6.75 (d, J =2.1 Hz, 1H), 6.78 (dd, J = 8.2, 2.1 Hz, 1H), 6.91 (d, J = 8.4 Hz, 1H),6.92-6.95 (m, 1H), 7.26 (d, J = 8.2 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(thiophen-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-18)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.02 (s, 3H),2.08 (s, 3H), 3.73 (s, 3H), 4.64 (d, J = 12.1 Hz, 1H), 5.09 (d, J = 12.1Hz, 1H), 5.40 (s, 1H), 6.03 (s, 1H), 6.37 (dd, J = 11.3, 2.4 Hz, 1H),6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.81 (d, J =8.2, 1H), 6.86 (dd, J = 8.2, 2.2 Hz, 1H), 7.01 (d, J = 2.2 Hz, 1H),7.03-7.06 (m, 1H), 7.22 (d, J = 8.2 Hz, 1H), 7.62 (dd, J = 5.0, 1.2 Hz,1H), 7.75 (dd, J = 5.0, 3.0 Hz, 1H), 8.60 (dd, J = 3.0, 1.2 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[4-(furan-2-ylcarbonyloxy)-2-methoxyphenyl]-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-19)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.02 (s, 3H),2.08 (s, 3H), 3.73 (s, 3H), 4.64 (d, J = 12.1 Hz, 1H), 5.09 (d, J = 12.1Hz, 1H), 5.40 (s, 1H), 6.03 (s, 1H), 6.37 (dd, J = 11.5, 2.4 Hz, 1H),6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.80 (d, J =8.2, 1H), 6.81 (dd, J = 3.6, 1.8 Hz, 1H), 6.86 (dd, J = 8.2, 2.2 Hz,1H), 7.02 (d, J = 2.2 Hz, 1H), 7.02-7.05 (m, 1H), 7.22 (d, J = 8.2 Hz,1H), 7.57 (d, J = 3.6 Hz, 1H), 8.11 (d, J = 1.8 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-(4-isobutyryloxy-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-20) 

¹H-NMR (400 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.15 (s, 3H), 1.24 (d, J = 7.0Hz, 6H), 2.01 (s, 3H), 2.07 (s, 3H), 2.81 (sept, J = 7.0 Hz, 1H), 3.72(s, 3H), 4.61 (d, J = 12.1 Hz, 1H), 5.07 (d, J = 12.1 Hz, 1H), 5.39 (s,1H), 6.03 (s, 1H), 6.35 (dd, J = 11.5, 2.5 Hz, 1H), 6.52 (td, J = 8.4,2.5 Hz, 1H), 6.63 (d, J = 8.3 Hz, 1H), 6.71 (dd, J = 8.3, 2.2 Hz, 1H),6.78 (d, J = 8.3 Hz, 1H), 6.83 (d, J = 2.2 Hz, 1H), 7.02- 7.05 (m, 1H),7.18 (d, J = 8.3 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-(2-methoxy-4-phenylacetoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-21)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.14 (s, 3H), 2.01 (s, 3H),2.06 (s, 3H), 3.71 (s, 3H), 3.96 (s, 2H), 4.60 (d, J = 12.2, 1H), 5.06(d, J = 12.2 Hz, 1H), 5.39 (s, 1H), 6.02 (s, 1H), 6.33 (dd, J = 11.5,2.5 Hz, 1H), 6.52 (td, J = 8.4, 2.5 Hz, 1H), 6.62 (d, J = 8.2 Hz, 1H),6.71 (dd, J = 8.1, 2.2 Hz, 1H), 6.77 (d, J = 8.2 Hz, 1H), 6.85 (d, J =2.2 Hz, 1H), 7.01-7.04 (m, 1H), 7.17 (d, J = 8.1 Hz, 1H), 7.28-7.32 (m,1H), 7.35- 7.40 (m, 4H)6-[5-(2-Chlorobenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-22)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.10 (s, 3H), 1.14 (s, 3H), 2.00 (s, 3H),2.06 (s, 3H), 3.76 (s, 3H), 4.64 (d, J = 12.0 Hz, 1H), 5.10 (d, J = 12.0Hz, 1H), 5.40 (s, 1H), 6.08 (s, 1H), 6.44 (dd, J = 11.2, 2.4 Hz, 1H),6.52 (td, J = 8.4, 2.4 Hz, 1H), 6.66 (d, J = 8.3 Hz, 1H), 6.84 (d, J =8.3 Hz, 1H), 6.98-7.02 (m, 1H), 7.11 (d, J = 2.9 Hz, 1H), 7.13 (d, J =8.9 Hz, 1H), 7.24 (dd, J = 8.9, 2.9 Hz, 1H), 7.54 (ddd, J = 8.1, 4.7,3.1 Hz, 1H), 7.65- 7.66 (m, 2H), 7.96-7.98 (m, 1H)6-[5-(3-Chlorobenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-23)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.12 (s, 3H), 1.13 (s, 3H), 1.99 (s, 3H),2.06 (s, 3H), 3.76 (s, 3H), 4.60 (d, J = 12.5 Hz, 1H), 5.09 (d, J = 12.5Hz, 1H), 5.40 (s, 1H), 6.07 (s, 1H), 6.46 (dd, J = 11.6, 2.5 Hz, 1H),6.53 (td, J = 8.3, 2.5 Hz, 1H), 6.65 (d, J = 8.2 Hz, 1H), 6.86 (d, J =8.2 Hz, 1H), 6.96-6.99 (m, 1H), 7.11 (d, J = 2.9 Hz, 1H), 7.12 (d, J =9.1 Hz, 1H), 7.23 (dd, J = 9.1, 2.9 Hz, 1H), 7.65 (t, J = 8.1 Hz, 1H),7.82 (d, J = 8.1 Hz, 1H), 8.00-8.01 (m, 2H)6-[5-(4-Chlorobenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-24)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.11 (s, 3H), 1.13 (s, 3H), 1.98 (s, 3H),2.06 (s, 3H), 3.76 (s, 3H), 4.61 (d, J = 11.9 Hz, 1H), 5.09 (d, J = 11.9Hz, 1H), 5.40 (s, 1H), 6.07 (s, 1H), 6.45 (dd, J = 11.5, 2.4 Hz, 1H),6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.3 Hz, 1H), 6.85 (d, J =8.3 Hz, 1H), 6.96-7.00 (m, 1H), 7.09 (d, J = 2.8 Hz, 1H), 7.12 (d, J =9.0 Hz, 1H), 7.22 (dd, J = 9.0, 2.8 Hz, 1H), 7.68 (dt, J = 9.1, 2.2 Hz,2H), 8.05 (dt, J = 9.1, 2.2 Hz, 2H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-5-(thiophen-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 1-25)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.10 (s, 3H), 1.13 (s, 3H), 1.98 (s, 3H),2.06 (s, 3H), 3.75 (s, 3H), 4.63 (d, J = 11.8 Hz, 1H), 5.09 (d, J = 11.8Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.43 (dd, J = 11.3, 2.4 Hz, 1H),6.52 (td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.84 (d, J =8.2 Hz, 1H), 6.97-7.00 (m, 1H), 7.05 (d, J = 2.9 Hz, 1H), 7.10 (d, J =8.9 Hz, 1H), 7.18 (dd, J = 8.9, 2.9 Hz, 1H), 7.54 (dd, J = 5.1, 1.2 Hz,1H), 7.73 (dd, J = 5.1, 3.0 Hz, 1H), 8.51 (dd, J = 3.0, 1.2 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[5-(furan-2-ylcarbonyloxy)-2-methoxyphenyl]-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-26)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.10 (s, 3H), 1.13 (s, 3H), 1.99 (s, 3H),2.06 (s, 3H), 3.75 (s, 3H), 4.64 (d, J = 12.3 Hz, 1H), 5.08 (d, J = 12.3Hz, 1H), 5.40 (s, 1H), 6.07 (s, 1H), 6.42 (dd, J = 11.5, 2.5 Hz, 1H),6.52 (td, J = 8.4, 2.5 Hz, 1H), 6.64 (d, J = 8.3 Hz, 1H), 6.79 (dd, J =3.6, 1.7 Hz, 1H), 6.83 (d, J = 8.3 Hz, 1H), 6.97-7.00 (m, 1H), 7.06 (d,J = 2.9 Hz, 1H), 7.10 (d, J = 8.9 Hz, 1H), 7.19 (dd, J = 8.9, 2.9 Hz,1H), 7.48 (dd, J = 3.6, 0.7 Hz, 1H), 8.08 (dd, J = 1.7, 0.7 Hz, 1H)5-(5-Fluoro-2-methylphenoxylmethyl)-6-(2-methoxy-5-propionyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-27)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.09 (t, J = 7.5 Hz, 3H), 1.09 (s, 3H), 1.13(s, 3H), 2.01 (s, 3H), 2.06 (s, 3H), 2.49-2.53 (m, 2H), 3.72 (s, 3H),4.60 (d, J = 11.9 Hz, 1H), 5.07 (d, J = 11.9 Hz, 1H), 5.40 (s, 1H), 6.05(s, 1H), 6.40 (dd, J = 11.5, 2.4 Hz, 1H), 6.53 (td, J = 8.4, 2.4 Hz,1H), 6.64 (d, J = 8.2 Hz, 1H), 6.80 (d, J = 8.2 Hz, 1H), 6.92 (d, J =2.4 Hz, 1H), 7.02- 7.06 (m, 3H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-5-(pyridin-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-28)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.12 (s, 3H), 1.13 (s, 3H), 1.98 (s, 3H),2.06 (s, 3H), 3.76 (s, 3H), 4.62 (d, J = 11.9 Hz, 1H), 5.09 (d, J = 11.9Hz, 1H), 5.40 (s, 1H), 6.08 (s, 1H), 6.46 (dd, J = 11.5, 2.4 Hz, 1H),6.52 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.2 Hz, 1H), 6.85 (d, J =8.2 Hz, 1H), 6.94-6.98 (m, 1H), 7.13 (d, J = 2.9 Hz, 1H), 7.13 (d, J =9.0 Hz, 1H), 7.25 (dd, J = 9.0, 2.9 Hz, 1H), 7.65 (ddd, J = 8.1, 4.9,1.1 Hz, 1H), 8.38 (dt, J = 8.1, 1.9 Hz, 1H), 8.89 (dd, J = 4.9, 1.9 Hz,1H), 9.18 (t, J = 1.1 Hz, 1H) 6-(5-Butyryloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-29)  

¹H-NMR (400 MHz, DMSO-d₆) δ 0.94 (t, J = 7.3 Hz, 3H), 1.09 (s, 3H), 1.14(s, 3H), 1.57-1.66 (m, 2H), 2.01 (s, 3H), 2.06 (s, 3H), 2.49-2.52 (m,2H), 3.72 (s, 3H), 4.59 (d, J = 12.0 Hz, 1H), 5.07 (d, J = 12.0 Hz, 1H),5.40 (s, 1H), 6.06 (s, 1H), 6.40 (dd, J = 11.5, 2.4 Hz, 1H), 6.53 (td, J= 8.4, 2.4 Hz, 1H), 6.63 (d, J = 8.3 Hz, 1H), 6.80 (d, J = 8.3 Hz, 1H),6.91 (d, J = 2.4 Hz, 1H), 7.01-7.07 (m, 3H)5-(5-Fluoro-2-methylphenoxymethyl)-6-(5-isobutyryloxy-2-methoxyphenyl)-2,2,4-trimethyl- 1,2-dihydroquinoline(Compound No. 1-30)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.08 (s, 3H), 1.14 (s, 3H), 1.17 (d, J = 7.1Hz, 6H), 2.01 (s, 3H), 2.06 (s, 3H), 2.73 (sept, J = 7.1 Hz, 1H), 3.72(s, 3H), 4.57 (d, J = 11.9 Hz, 1H), 5.08 (d, J = 11.9 Hz, 1H), 5.40 (s,1H), 6.06 (s, 1H), 6.40 (dd, J = 11.5, 2.4 Hz, 1H), 6.53 (td, J = 8.4,2.4 Hz, 1H), 6.64 (d, J = 8.1 Hz, 1H), 6.80 (d, J = 8.1 Hz, 1H), 6.90(d, J = 2.7 Hz, 1H), 7.01-7.07 (m, 3H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(thiophen-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 1-31)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.02 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.64 (d, J = 12.1 Hz, 1H), 5.09 (d, J = 12.1Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.37 (dd, J = 11.5, 2.4 Hz, 1H),6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.3 Hz, 1H), 6.81 (d, J =8.3 Hz, 1H), 6.88 (dd, J = 8.2, 2.2 Hz, 1H), 7.03 (d, J = 2.2 Hz, 1H),7.02-7.06 (m, 1H), 7.23 (d, J = 8.2 Hz, 1H), 7.32 (dd, J = 5.0, 3.9 Hz,1H), 8.03 (dd, J = 3.9, 1.3 Hz, 1H), 8.10 (dd, J = 5.0, 1.3 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-(2-methoxy-5-phenylacetoxyphenyl)-2,2,4-trimethyl-1,2- dihydroquinoline (Compound No.1-32)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.09 (s, 3H), 1.13 (s, 3H), 1.99 (s, 3H),2.05 (s, 3H), 3.72 (s, 3H), 3.88 (s, 2H), 4.58 (d, J = 11.9 Hz, 1H),5.06 (d, J = 11.9 Hz, 1H), 5.39 (s, 1H), 6.06 (s, 1H), 6.39 (dd, J =11.5, 2.4 Hz, 1H), 6.53 (td, J = 8.5, 2.4 Hz, 1H), 6.63 (d, J = 8.3 Hz,1H), 6.78 (d, J = 8.3 Hz, 1H), 6.90 (d, J = 2.0 Hz, 1H), 7.01-7.05 (m,3H), 7.28-7.38 (m, 5H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3-phenylpropionyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 1-33)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.14 (s, 3H), 2.01 (s, 3H),2.06 (s, 3H), 2.88-2.92 (m, 2H), 2.96- 3.00 (m, 2H), 3.69 (s, 3H), 4.60(d, J = 12.1 Hz, 1H), 5.06 (d, J = 12.1 Hz, 1H), 5.39 (s, 1H), 6.03 (s,1H), 6.34 (dd, J = 11.5, 2.4 Hz, 1H), 6.52 (td, J = 8.4, 2.4 Hz, 1H),6.63 (d, J = 8.2 Hz, 1H), 6.64 (dd, J = 8.1, 2.2 Hz, 1H), 6.73 (d, J =2.2 Hz, 1H), 6.77 (d, J = 8.2 Hz, 1H), 7.01-7.05 (m, 1H), 7.16 (d, J =8.1 Hz, 1H), 7.20- 7.24 (m, 1H), 7.29-7.34 (m, 4H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[4-(furan-3-ylcarbonyloxy)-2-methoxyphenyl]-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-34)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.02 (s, 3H),2.07 (s, 3H), 3.73 (s, 3H), 4.62 (d, J = 12.2 Hz, 1H), 5.08 (d, J = 12.2Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.37 (dd, J = 11.5, 2.4 Hz, 1H),6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.80 (d, J =8.2 Hz, 1H), 6.84 (dd, J = 8.2, 2.2 Hz, 1H), 6.94 (dd, J = 1.7, 0.9 Hz,1H), 6.98 (d, J = 2.2 Hz, 1H), 7.02-7.06 (m, 1H), 7.22 (d, J = 8.2 Hz,1H), 7.92 (t, J = 1.7 Hz, 1H), 8.64 (dd, J = 1.7, 0.9 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(pyridin-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-35)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.66 (d, J = 12.2 Hz, 1H), 5.10 (d, J = 12.2Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.38 (dd, J = 11.5, 2.4 Hz, 1H),6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.2 Hz, 1H), 6.82 (d, J =8.2 Hz, 1H), 6.91 (dd, J = 8.2, 2.2 Hz, 1H), 7.03-7.06 (m, 1H), 7.06 (d,J = 2.2 Hz, 1H), 7.25 (d, J = 8.2 Hz, 1H), 7.74 (ddd, J = 7.7, 4.7, 1.1Hz, 1H), 8.09 (td, J = 7.7, 1.7 Hz, 1H), 8.25 (dt, J = 7.7, 1.1 Hz, 1H),8.82 (ddd, J = 4.7, 1.7, 1.1 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-5-(thiophen-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-36)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.11 (s, 3H), 1.13 (s, 3H), 1.99 (s, 3H),2.06 (s, 3H), 3.75 (s, 3H), 4.61 (d, J = 12.4 Hz, 1H), 5.09 (d, J = 12.4Hz, 1H), 5.40 (s, 1H), 6.07 (s, 1H), 6.44 (dd, J = 11.4, 2.5 Hz, 1H),6.52 (td, J = 8.4, 2.5 Hz, 1H), 6.64 (d, J = 8.3 Hz, 1H), 6.84 (d, J =8.3 Hz, 1H), 6.96-7.01 (m, 1H), 7.07 (d, J = 2.9 Hz, 1H), 7.10 (d, J =8.9 Hz, 1H), 7.20 (dd, J = 8.9, 2.9 Hz, 1H), 7.30 (dd, J = 5.0, 3.8 Hz,1H), 7.94 (dd, J = 3.8, 1.3 Hz, 1H), 8.07 (dd, J = 5.0, 1.3 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[5-(furan-3-ylcarbonyloxy)-2-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-37)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.10 (s, 3H), 1.13 (s, 3H), 1.99 (s, 3H),2.06 (s, 3H), 3.74 (s, 3H), 4.63 (d, J = 12.4 Hz, 1H), 5.08 (d, J = 12.4Hz, 1H), 5.40 (s, 1H), 6.07 (s, 1H), 6.42 (dd, J = 11.5, 2.5 Hz, 1H),6.53 (td, J = 8.5, 2.5 Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.83 (d, J =8.2 Hz, 1H), 6.87 (dd, J = 1.7, 0.9 Hz, 1H), 6.98- 7.01 (m, 1H), 7.04(d, J = 2.9 Hz, 1H), 7.10 (d, J = 9.0 Hz, 1H), 7.17 (dd, J = 9.0, 2.9Hz, 1H), 7.89 (t, J = 1.7 Hz, 1H), 8.55 (dd, J = 1.7, 0.9 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-nitrobenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 1-38)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.02 (s, 3H),2.07 (s, 3H), 3.75 (s, 3H), 4.64 (d, J = 12.2 Hz, 1H), 5.09 (d, J =12.2Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.38 (dd, J = 11.4, 2.3 Hz, 1H),6.53 (td, J = 8.5, 2.3 Hz, 1H), 6.65 (d, J = 8.2 Hz, 1H), 6.81 (d, J =8.2 Hz, 1H), 6.88 (dd, J = 8.3, 2.2 Hz, 1H), 7.02 (d, J = 2.2 Hz, 1H),7.02- 7.06 (m, 1H), 7.28 (d, J = 8.3 Hz, 1H), 7.92 (td, J = 7.7, 1.4 Hz,1H), 7.96 (td, J = 7.7, 1.4 Hz, 1H), 8.13 (dd, J = 7.7, 1.4 Hz, 1H),8.19 (dd, J = 7.7, 1.4 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3-nitrobenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 1-39)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.75 (s, 3H), 4.65 (d, J = 12.1 Hz, 1H), 5.11 (d, J =12.1Hz, 1H), 5.41 (s, 1H), 6.06 (s, 1H), 6.39 (dd, J = 11.5, 2.4 Hz, 1H),6.54 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.3 Hz, 1H), 6.82 (d, J =8.3 Hz, 1H), 6.95 (dd, J = 8.3, 2.2 Hz, 1H), 7.03-7.07 (m, 1H), 7.13 (d,J = 2.2 Hz, 1H), 7.26 (d, J = 8.3 Hz, 1H), 7.93 (t, J = 7.9 Hz, 1H),8.54- 8.56 (m, 1H), 8.58-8.61 (m, 1H), 8.81 (t, J = 2.0 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-nitrobenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 1-40)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.65 (d, J = 12.1 Hz, 1H), 5.10 (d, J =12.1Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.38 (dd, J = 11.4, 2.3 Hz, 1H),6.54 (td, J = 8.4, 2.3 Hz, 1H), 6.65 (d, J = 8.3 Hz, 1H), 6.82 (d, J =8.3 Hz, 1H), 6.95 (dd, J = 8.3, 2.2 Hz, 1H), 7.03-7.06 (m, 1H), 7.12 (d,J = 2.2 Hz, 1H), 7.26 (d, J = 8.3 Hz, 1H), 8.38 (d, J = 9.0 Hz, 2H),8.43 (d, J = 9.0 Hz, 2H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-trifluoromethylbenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-41)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.02 (s, 3H),2.08 (s, 3H), 3.76 (s, 3H), 4.65 (d, J = 12.1 Hz, 1H), 5.10 (d, J =12.1Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.38 (dd, J = 11.4, 2.4 Hz, 1H),6.53 (td, J = 8.3, 2.4 Hz, 1H), 6.65 (d, J = 8.3 Hz, 1H), 6.81 (d, J =8.3 Hz, 1H), 6.88 (dd, J = 8.2, 2.3 Hz, 1H), 7.02- 7.06 (m, 1H), 7.04(d, J = 2.3 Hz, 1H), 7.27 (d, J = 8.2 Hz, 1H), 7.86-7.93 (m, 2H),7.97-8.00 (m, 1H), 8.15 (d, J = 7.1 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-(2-methoxy-4-methoxyacetoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-42)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.15 (s, 3H), 2.01 (s, 3H),2.07 (s, 3H), 3.40 (s, 3H), 3.72 (s, 3H), 4.33 (s, 2H), 4.61 (d, J =12.2 Hz, 1H), 5.07 (d, J =12.2 Hz, 1H), 5.39 (s, 1H), 6.04 (s, 1H), 6.35(dd, J = 11.5, 2.5 Hz, 1H), 6.52 (td, J = 8.4, 2.5 Hz, 1H), 6.63 (d, J =8.4 Hz, 1H), 6.77 (dd, J = 8.1, 2.1 Hz, 1H), 6.78 (d, J = 8.4 Hz, 1H),6.91 (d, J = 2.1 Hz, 1H), 7.01-7.05 (m, 1H), 7.19 (d, J = 8.1 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(pyridin-4-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-43)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.64 (d, J = 12.1 Hz, 1H), 5.10 (d, J =12.1Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.38 (dd, J = 11.3, 2.4 Hz, 1H),6.54 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.2 Hz, 1H), 6.81 (d, J =8.2 Hz, 1H), 6.93 (dd, J = 8.2, 2.4 Hz, 1H), 7.03-7.06 (m, 1H), 7.11 (d,J = 2.4 Hz, 1H), 7.25 (d, J = 8.2 Hz, 1H), 8.02 (d, J = 6.0 Hz, 2H),8.89 (d, J = 6.0 Hz, 2H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-5-(pyridin-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-44)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.10 (s, 3H), 1.13 (s, 3H), 1.98 (s, 3H),2.06 (s, 3H), 3.76 (s, 3H), 4.67 (d, J = 12.0 Hz, 1H), 5.09 (d, J =12.0Hz, 1H), 5.40 (s, 1H), 6.08 (s, 1H), 6.43 (dd, J = 11.6, 2.4 Hz, 1H),6.52 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.3 Hz, 1H), 6.85 (d, J =8.3 Hz, 1H), 6.95-6.99 (m, 1H), 7.11 (d, J = 2.9 Hz, 1H), 7.13 (d, J =9.0 Hz, 1H), 7.23 (dd, J = 9.0, 2.9 Hz, 1H), 7.73 (ddd, J = 7.7, 4.8,1.1 Hz, 1H), 8.07 (td, J = 7.7, 1.7 Hz, 1H), 8.15 (dt, J = 7.7, 1.1 Hz,1H), 8.80 (ddd, J = 4.8, 1.7, 1.1 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-5-(pyridin-4-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-45)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.12 (s, 3H), 1.13 (s, 3H), 1.98 (s, 3H),2.06 (s, 3H), 3.76 (s, 3H), 4.61 (d, J = 11.8 Hz, 1H), 5.09 (d, J =11.8Hz, 1H), 5.40 (s, 1H), 6.09 (s, 1H), 6.45 (dd, J = 11.4, 2.4 Hz, 1H),6.53 (td, J = 8.3, 2.4 Hz, 1H), 6.65 (d, J = 8.3 Hz, 1H), 6.85 (d, J =8.3 Hz, 1H), 6.96-6.99 (m, 1H), 7.13 (d, J = 2.9 Hz, 1H), 7.13 (d, J =9.0 Hz, 1H), 7.26 (dd, J = 9.0, 2.9 Hz, 1H), 7.92 (d, J = 6.1 Hz, 2H),8.88 (d, J = 6.1 Hz, 2H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-naphtylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 1-46)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.07 (s, 3H), 1.16 (s, 3H), 2.04 (s, 3H),2.09 (s, 3H), 3.75 (s, 3H), 4.66 (d, J = 12.1 Hz, 1H), 5.11 (d, J =12.1Hz, 1H), 5.41 (s, 1H), 6.05 (s, 1H), 6.40 (dd, J = 11.5, 2.4 Hz, 1H),6.55 (td, J = 8.4, 2.4 Hz, 1H), 6.66 (d, J = 8.2 Hz, 1H), 6.84 (d, J =8.2 Hz, 1H), 6.95 (dd, J = 8.2, 2.4 Hz, 1H), 7.04-7.07 (m, 1H), 7.11 (d,J = 2.4 Hz, 1H), 7.27 (d, J = 8.2 Hz, 1H), 7.65- 7.69 (m, 1H), 7.71-7.75(m, 1H), 8.08 (d, J = 8.3 Hz, 1H), 8.12-8.15 (m, 2H), 8.22 (d, J = 8.0Hz, 1H), 8.87 (s, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(1-naphtylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-47)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.19 (s, 3H), 2.05 (s, 3H),2.09 (s, 3H), 3.77 (s, 3H), 4.68 (d, J = 12.4 Hz, 1H), 5.13 (d, J =12.4Hz, 1H), 5.41 (s, 1H), 6.06 (s, 1H), 6.40 (dd, J = 11.7, 2.4 Hz, 1H),6.54 (td, J = 8.4, 2.4 Hz, 1H), 6.67 (d, J = 8.2 Hz, 1H), 6.84 (d, J =8.2 Hz, 1H), 6.99 (dd, J = 8.2, 2.1 Hz, 1H), 7.04- 7.07 (m, 1H), 7.11(d, J = 2.1 Hz, 1H), 7.28 (d, J = 8.2 Hz, 1H), 7.64-7.74 (m, 3H), 8.11(d, J = 7.3 Hz, 1H), 8.31 (d, J = 8.1 Hz, 1H), 8.47 (d, J = 7.3 Hz, 1H),8.86 (d, J = 8.3 Hz, 1H) 6-(5-Benzoyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline (Compound No.1-48)  

¹H-NMR (500 MHz, CDCl₃) δ 1.16 (s, 3H), 1.23 (s, 3H), 2.05 (s, 3H), 2.15(s, 3H), 3.77 (s, 3H), 3.87 (br s, 1H), 4.77 (d, J = 11.9 Hz, 1H), 5.12(d, J = 11.9 Hz, 1H), 5.46 (s, 1H), 6.27 (dd, J = 11.3, 2.4 Hz, 1H),6.43 (td, J = 8.2, 2.4 Hz, 1H), 6.59 (d, J = 8.2 Hz, 1H), 6.89-6.92 (m,1H), 6.96 (d, J = 8.8 Hz, 1H), 6.97 (d, J = 8.2 Hz, 1H), 7.13 (d, J =3.1 Hz, 1H), 7.17 (dd, J = 8.8, 3.1 Hz, 1H), 7.50 (t, J = 7. 8 Hz, 2H),7.62 (t, J = 7.8 Hz, 1H), 8.16 (d, J = 7.8 Hz, 2H)6-[4-(3-Dimethylaminobenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-49)  

¹H-NMR (400 MHz, CDCl₃) δ 1.13 (s, 3H), 1.24 (s, 3H), 2.08 (s, 3H), 2.16(s, 3H), 3.03 (s, 6H), 3.77 (s, 3H), 4.78 (d, J = 12.1 Hz, 1H), 5.13 (d,J = 12.1 Hz, 1H), 5.46 (s, 1H), 6.22 (dd, J = 11.2, 2.4 Hz, 1H), 6.43(td, J = 8.3, 2.4 Hz, 1H), 6.60 (d, J = 8.2 Hz, 1H), 6.84 (d, J = 2.2Hz, 1H), 6.86 (dd, J = 8.1, 2.2 Hz, 1H), 6.94 (d, J = 8.2 Hz, 1H),6.92-6.96 (m, 1H), 6.98 (d, J = 8.0 Hz, 1H), 7.30 (d, J = 8.1 Hz, 1H),7.37 (t, J = 8.0 Hz, 1H), 7.52-7.57 (m, 2H)6-[4-(2-Acetoxybenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-50)  

¹H-NMR (500 MHz, CDCl₃) δ 1.13 (s, 3H), 1.23 (s, 3H), 2.08 (s, 3H), 2.17(s, 3H), 2.32 (s, 3H), 3.76 (s, 3H), 4.75 (d, J = 11.9 Hz, 1H), 5.12 (d,J = 11.9 Hz, 1H), 5.46 (s, 1H), 6.21 (dd, J = 11.0, 2.4 Hz, 1H), 6.43(td, J = 8.4, 2.4 Hz, 1H), 6.59 (d, J = 8.1 Hz, 1H), 6.78 (d, J = 2.1Hz, 1H), 6.81 (dd, J = 8.1, 2.1 Hz, 1H), 6.92 (d, J = 8.1 Hz, 1H),6.93-6.95 (m, 1H), 7.19 (dd, J = 7.9, 1.4 Hz, 1H), 7.29 (d, J = 8.1 Hz,1H), 7.40 (td, J = 7.9, 1.4 Hz, 1H), 7.65 (td, J = 7.9, 1.4 Hz, 1H),8.24 (dd, J = 7.9, 1.4 Hz, 1H)6-[4-(1-t-Butoxycarbonylpiperidin-4-ylcarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 1-51)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.15 (s, 3H), 1.53-1.62 (m,2H), 1.95-1.96 (m, 2H), 2.01 (s, 3H), 2.07 (s, 3H), 2.81-2.84 (m, 1H),2.91- 2.93 (m 2H), 3.72 (s, 3H), 3.89-3.92 (m, 2H), 4.61 (d, J = 12.1Hz, 1H), 5.07 (d, J = 12.1 Hz, 1H), 5.39 (s, 1H), 6.03 (s, 1H), 6.34(dd, J = 11.5, 2.4 Hz, 1H), 6.52 (td, J = 8.4, 2.4 Hz, 1H), 6.63 (d, J =8.1 Hz, 1H), 6.73 (dd, J = 8.3, 2.2 Hz, 1H), 6.78 (d, J = 8.1 Hz, 1H),6.86 (d, J = 2.2 Hz, 1H), 7.01-7.05 (m, 1H), 7.18 (d, J = 8.3 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-methylthiobenzoyloxy)phenyl]-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-52)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 2.47 (s, 3H), 3.74 (s, 3H), 4.66 (d, J = 12.2 Hz, 1H),5.11 (d, J = 12.2 Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.38 (dd, J =11.5, 2.4 Hz, 1H), 6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.2 Hz,1H), 6.81 (d, J = 8.2 Hz, 1H), 6.87 (dd, J = 8.0, 2.4 Hz, 1H), 7.02 (d,J = 2.4 Hz, 1H), 7.03- 7.06 (m, 1H), 7.24 (d, J = 8.0 Hz, 1H), 7.31-7.35(m, 1H), 7.47 (d, J = 7.9 Hz, 1H), 7.66-7.69 (m, 1H), 8.19 (dd, J = 7.6,1.5 Hz, 1H)6-[4-(1-t-Butoxycarbonylimidazol-4-ylcarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 1-53)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 1.61 (s, 9H),2.02 (s, 3H), 2.08 (s, 3H), 3.73 (s, 3H), 4.63 (d, J = 12.1 Hz, 1H),5.09 (d, J = 12.1 Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.37 (dd, J =11.5, 2.4 Hz, 1H), 6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.3 Hz,1H), 6.81 (d, J = 8.3 Hz, 1H), 6.85 (dd, J = 8.3, 2.2 Hz, 1H), 6.99 (d,J = 2.2 Hz, 1H), 7.02- 7.06 (m, 1H), 7.22 (d, J = 8.3 Hz, 1H), 8.37 (d,J = 1.2 Hz, 1H), 8.41 (d, J = 1.2 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(thiazol-4-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 1-54)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.02 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.64 (d, J = 12.1 Hz, 1H), 5.10 (d, J = 12.1Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.37 (dd, J = 11.2, 2.5 Hz, 1H),6.53 (td, J = 8.4, 2.5 Hz, 1H), 6.65 (d, J = 8.3 Hz, 1H), 6.82 (d, J =8.3 Hz, 1H), 6.89 (dd, J = 8.3, 2.2 Hz, 1H), 7.02-7.06 (m, 1H), 7.04 (d,J = 2.2 Hz, 1H), 7.24 (d, J = 8.3 Hz, 1H), 8.88 (d, J = 1.9 Hz, 1H),9.28 (d, J = 1.9 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(thiazol-5-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-55)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.02 (s, 3H),2.07 (s, 3H), 3.74 (s, 3H), 4.63 (d, J = 12.2 Hz, 1H), 5.09 (d, J = 12.2Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.38 (dd, J = 11.2, 2.5 Hz, 1H),6.53 (td, J = 8.5, 2.5 Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.81 (d, J =8.2 Hz, 1H), 6.91 (dd, J = 8.2, 2.2 Hz, 1H), 7.02-7.06 (m, 1H), 7.08 (d,J = 2.2 Hz, 1H), 7.24 (d, J = 8.2 Hz, 1H), 8.76 (d, J = 0.7 Hz, 1H),9.49 (d, J = 0.7 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(oxazol-4-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 1-56)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.02 (s, 3H),2.08 (s, 3H), 3.73 (s, 3H), 4.63 (d, J = 12.4 Hz, 1H), 5.09 (d, J = 12.4Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.37 (dd, J = 11.5, 2.4 Hz, 1H),6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.81 (d, J =8.2 Hz, 1H), 6.86 (dd, J = 8.2, 2.3 Hz, 1H), 7.01 (d, J = 2.3 Hz, 1H),7.02-7.06 (m, 1H), 7.23 (d, J = 8.2 Hz, 1H), 8.67 (d, J = 1.0 Hz, 1H),9.14 (d, J = 1.0 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(5-methylthiophen-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-57)  

¹H-NMR (400 MHz, Solv. DMSO-d₆) δ 1.05 (s, 3H), 1.15 (s, 3H), 2.02 (s,3H), 2.07 (s, 3H), 2.57 (s, 3H), 3.74 (s, 3H), 4.63 (d, J = 12.1 Hz,1H), 5.09 (d, J = 12.1 Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.37 (dd, J= 11.4, 2.5 Hz, 1H), 6.53 (td, J = 8.4, 2.5 Hz, 1H), 6.64 (d, J = 8.3Hz, 1H), 6.80 (d, J = 8.3 Hz, 1H), 6.85 (dd, J = 8.3, 2.4 Hz, 1H), 7.00(d, J = 2.4 Hz, 1H), 7.02-7.06 (m, 2H), 7.22 (d, J = 8.3 Hz, 1H), 7.85(d, J = 3.4 Hz, 1H)6-[4-(3-Acetylbenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-58)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 2.68 (s, 3H), 3.75 (s, 3H), 4.65 (d, J = 12.2 Hz, 1H),5.11 (d, J = 12.2 Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.39 (dd, J =11.3, 2.4 Hz, 1H), 6.54 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.1 Hz,1H), 6.82 (d, J = 8.1 Hz, 1H), 6.93 (dd, J = 8.1, 2.1 Hz, 1H), 7.03-7.06 (m, 1H), 7.09 (d, J = 2.1 Hz, 1H), 7.25 (d, J = 8.1 Hz, 1H), 7.79(t, J = 7.9 Hz, 1H), 8.32 (dt, J = 7.9, 1.5 Hz, 1H), 8.38 (dt, J = 7.9,1.5 Hz, 1H), 8.68 (t, J =1.5 Hz, 1H)6-[4-(2-Fluorobenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-59)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.65 (d, J = 12.1 Hz, 1H), 5.10 (d, J = 12.1Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.38 (dd, J = 11.4, 2.4 Hz, 1H),6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.3 Hz, 1H), 6.81 (d, J =8.3 Hz, 1H), 6.90 (dd, J = 8.2, 2.2 Hz, 1H), 7.02-7.06 (m, 1H), 7.06 (d,J = 2.2 Hz, 1H), 7.24 (d, J = 8.2 Hz, 1H), 7.41-7.47 (m, 2H), 7.76-7.81(m, 1H), 8.12 (td, J = 7.8, 1.7 Hz, 1H)6-[4-(3-Fluorobenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-60)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.64 (d, J = 12.2 Hz, 1H), 5.10 (d, J = 12.2Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.38 (dd, J = 11.4, 2.5 Hz, 1H),6.54 (td, J = 8.2, 2.5 Hz, 1H), 6.65 (d, J = 8.2 Hz, 1H), 6.81 (d, J =8.2 Hz, 1H), 6.91 (dd, J = 8.2, 2.2 Hz, 1H), 7.02- 7.06 (m, 1H), 7.08(d, J = 2.2 Hz, 1H), 7.25 (d, J = 8.2 Hz, 1H), 7.63 (tdd, J = 8.5, 2.6,1.2 Hz, 1H), 7.66-7.71 (m, 1H), 7.88- 7.91 (m, 1H), 8.00 (dt, J = 7.5,1.4 Hz, 1H) 6-[4-(4-Fluorobenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-61)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.65 (d, J = 12.2 Hz, 1H), 5.10 (d, J = 12.2Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.38 (dd, J = 11.3, 2.4 Hz, 1H),6.54 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.2 Hz, 1H), 6.81 (d, J =8.2 Hz, 1H), 6.89 (dd, J = 8.1, 2.1 Hz, 1H), 7.03- 7.06 (m, 1H), 7.06(d, J = 2.1 Hz, 1H), 7.24 (d, J = 8.1 Hz, 1H), 7.44-7.47 (m, 2H),8.20-8.23 (m, 2H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(5-methylfuran-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 1-62)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.02 (s, 3H),2.07 (s, 3H), 2.42 (s, 3H), 3.73 (s, 3H), 4.63 (d, J = 12.0 Hz, 1H),5.08 (d, J = 12.0 Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.37 (dd, J =11.5, 2.4 Hz, 1H), 6.45 (d, J = 3.4, Hz, 1H), 6.53 (td, J = 8.4, 2.4 Hz,1H), 6.64 (d, J = 8.1 Hz, 1H), 6.80 (d, J = 8.1 Hz, 1H), 6.84 (dd, J =8.3, 2.3 Hz, 1H) 6.98 (d, J = 2.3 Hz, 1H), 7.02-7.06 (m, 1H), 7.21 (d, J= 8.3 Hz, 1H), 7.47 (d, J = 3.4 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-methylpyridin-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-63)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 2.80 (s, 3H), 3.75 (s, 3H), 4.65 (d, J = 12.1 Hz, 1H),5.11 (d, J = 12.1 Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.38 (dd, J =11.2, 2.4 Hz, 1H), 6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.1 Hz,1H), 6.81 (d, J = 8.1 Hz, 1H), 6.92 (dd, J = 8.2, 2.3 Hz, 1H) 7.03-7.06(m, 1H), 7.09 (d, J = 2.3 Hz, 1H), 7.47 (dd, J = 7.9, 4.7 Hz, 1H), 8.45(dd, J = 7.9, 1.7 Hz, 1H), 8.72 (dd, J = 4.7, 1.7 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(pyridin-3-ylacetoxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-64)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.14 (s, 3H), 2.01 (s, 3H),2.06 (s, 3H), 3.71 (s, 3H), 4.05 (s, 2H), 4.60 (d, J = 12.1 Hz, 1H),5.07 (d, J = 12.1 Hz, 1H), 5.39 (s, 1H), 6.04 (s, 1H), 6.34 (dd, J =11.5, 2.4 Hz, 1H), 6.52 (td, J = 8.5, 2.4 Hz, 1H), 6.62 (d, J = 8.2 Hz,1H), 6.75 (dd, J = 8.2, 2.3 Hz, 1H) 6.78 (d, J = 8.2 Hz, 1H), 6.89 (d, J= 2.3 Hz, 1H), 7.01-7.05 (m, 1H), 7.18 (d, J = 8.2 Hz, 1H), 7.40 (dd, J= 7.8, 4.8 Hz, 1H), 7.47 (dt, J = 7.8, 2.0 Hz, 1H), 8.50 (dd, J = 4.8,2.0 Hz, 1H), 8.59 (d, J = 2.0 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3-methylthiophen-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 1-65)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.15 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 2.56 (s, 3H), 3.74 (s, 3H), 4.65 (d, J = 12.1 Hz, 1H),5.10 (d, J = 12.1 Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.37 (dd, J =11.5, 2.5 Hz, 1H), 6.53 (td, J = 8.4, 2.5 Hz, 1H), 6.64 (d, J = 8.2 Hz,1H), 6.80 (d, J = 8.2 Hz, 1H) 6.85 (dd, J = 8.2 , 2.2 Hz, 1H), 7.00 (d,J = 2.2 Hz, 1H), 7.03-7.06 (m, 1H), 7.17 (d, J = 5.1 Hz, 1H), 7.22 (d, J= 8.2 Hz, 1H), 7.93 (d, J = 5.1 Hz, 1H)5-(5-Fluoro-2-methylphenoxylmethyl)-6-[2-methoxy-4-(4-methylthiophen-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-66)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.07 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 2.30 (s, 3H), 3.74 (s, 3H), 4.64 (d, J = 12.4 Hz, 1H),5.10 (d, J = 12.4 Hz, 1H), 5.41 (s, 1H), 6.05 (s, 1H), 6.38 (dd, J =11.3, 2.5 Hz, 1H), 6.54 (td, J = 8.5, 2.5 Hz, 1H), 6.65 (d, J = 8.2 Hz,1H), 6.81 (d, J = 8.2 Hz, 1H), 6.87 (dd, J = 8.2 , 2.2 Hz, 1H), 7.02 (d,J = 2.2 Hz, 1H), 7.04-7.07 (m, 1H), 7.23 (d, J = 8.2 Hz, 1H), 7.69-7.70(m, 1H), 7.87 (d, J = 1.2 Hz, 1H)6-[4-(4-Acetylbenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-67)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 2.67 (s, 3H), 3.74 (s, 3H), 4.65 (d, J = 12.2 Hz, 1H),5.10 (d, J = 12.2 Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.38 (dd, J =11.5, 2.4 Hz, 1H), 6.54 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.2 Hz,1H), 6.82 (d, J = 8.2 Hz, 1H) 6.92 (dd, J = 8.3, 2.2 Hz, 1H), 7.03-7.07(m, 1H), 7.09 (d, J = 2.2 Hz, 1H), 7.25 (d, J = 8.3 Hz, 1H), 8.14-8.17(m, 2H), 8.25- 8.28 (m, 2H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3-methoxycarbonylbenzoyloxy)phenyl]-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-68)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 3.92 (s, 3H), 4.65 (d, J = 12.2 Hz, 1H),5.11 (d, J = 12.2 Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.39 (dd, J =11.5, 2.4 Hz, 1H), 6.54 (td, J = 8.3, 2.4 Hz, 1H), 6.65 (d, J = 8.2 Hz,1H), 6.82 (d, J = 8.2 Hz, 1H) 6.93 (dd, J = 8.2, 2.2 Hz, 1H), 7.03-7.06(m, 1H), 7.10 (d, J = 2.2 Hz, 1H), 7.25 (d, J = 8.2 Hz, 1H), 7.79 (t, J= 7.9 Hz, 1H), 8.31 (dt, J = 7.9, 1.6 Hz, 1H), 8.40 (dt, J = 7.9, 1.6Hz, 1H), 8.66 (t, J = 1.6 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(6-methylpyridin-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-69)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 2.61 (s, 3H), 3.74 (s, 3H), 4.64 (d, J = 12.2 Hz, 1H),5.10 (d, J = 12.2 Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.38 (dd, J =11.4, 2.4 Hz, 1H), 6.54 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.3 Hz,1H), 6.82 (d, J = 8.3 Hz, 1H), 6.91 (dd, J = 8.1, 2.2 Hz, 1H), 7.03-7.06 (m, 1H), 7.08 (d, J = 2.2 Hz, 1H), 7.24 (d, J = 8.1 Hz, 1H), 7.51(d, J = 8.1 Hz, 1H), 8.35 (dd, J = 8.1, 2.2 Hz, 1H), 9.14 (d, J = 2.2Hz, 1H) 5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-methylpyridin-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-70)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.07 (s, 3H), 1.16 (s, 3H), 2.04 (s, 3H),2.09 (s, 3H), 2.64 (s, 3H), 3.76 (s, 3H), 4.66 (d, J = 12.2 Hz, 1H),5.11 (d, J = 12.2 Hz, 1H), 5.41 (s, 1H), 6.05 (s, 1H), 6.39 (dd, J =11.3, 2.4 Hz, 1H), 6.54 (td, J = 8.4, 2.4 Hz, 1H), 6.66 (d, J = 8.1 Hz,1H), 6.82 (d, J = 8.1 Hz, 1H), 6.95 (dd, J = 8.0, 2.2 Hz, 1H), 7.04-7.07 (m, 1H), 7.12 (d, J = 2.2 Hz, 1H), 7.26 (d, J = 8.0 Hz, 1H), 7.48(d, J = 5.1 Hz, 1H), 8.69 (d, J = 5.1 Hz, 1H), 9.19 (s, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3-methylfuran-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-71)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.15 (s, 3H), 2.02 (s, 3H),2.08 (s, 3H), 2.38 (s, 3H), 3.73 (s, 3H), 4.65 (d, J = 12.2 Hz, 1H),5.10 (d, J = 12.2 Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.37 (dd, J =11.4, 2.5 Hz, 1H), 6.53 (td, J = 8.4, 2.5 Hz, 1H), 6.64 (d, J = 8.2 Hz,1H), 6.70 (d, J = 1.7 Hz, 1H), 6.80 (d, J = 8.2 Hz, 1H), 6.86 (dd, J =8.3, 2.2 Hz, 1H), 7.01 (d, J = 2.2 Hz, 1H), 7.02- 7.06 (m, 1H), 7.22 (d,J = 8.3 Hz, 1H), 7.96 (d, J = 1.7 Hz, 1H)6-(4-t-Butylcarbonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-72)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.15 (s, 3H), 1.31 (s, 9H),2.02 (s, 3H), 2.06 (s, 3H), 3.73 (s, 3H), 4.61 (d, J = 12.2 Hz, 1H),5.07 (d, J = 12.2 Hz, 1H), 5.39 (s, 1H), 6.03 (s, 1H), 6.35 (dd, J =11.3, 2.4 Hz, 1H), 6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.63 (d, J = 8.2 Hz,1H), 6.69 (dd, J = 8.1, 2.3 Hz, 1H), 6.78 (d, J = 8.2 Hz, 1H), 6.81 (d,J = 2.3 Hz, 1H), 7.02-7.05 (m, 1H), 7.18 (d, J = 8.1 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-trifluoromethoxybenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 1-73)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.65 (d, J = 12.1 Hz, 1H), 5.10 (d, J = 12.1Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.38 (dd, J = 11.5, 2.4 Hz, 1H),6.54 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.2 Hz, 1H), 6.82 (d, J =8.2 Hz, 1H), 6.91 (dd, J = 8.2, 2.2 Hz, 1H), 7.02- 7.06 (m, 1H), 7.07(d, J = 2.2 Hz, 1H), 7.25 (d, J = 8.2 Hz, 1H), 7.59-7.62 (m, 2H),8.26-8.29 (m, 2H)6-[4-(Benzothiophen-2-ylcarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 1-74)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.76 (s, 3H), 4.65 (d, J = 12.2 Hz, 1H), 5.11 (d, J = 12.2Hz, 1H), 5.41 (s, 1H), 6.06 (s, 1H), 6.39 (dd, J = 11.5, 2.4 Hz, 1H),6.54 (td, J = 8.4, 2.4 Hz, 1H), 6.66 (d, J = 8.3 Hz, 1H), 6.82 (d, J =8.3 Hz, 1H), 6.94 (dd, J = 8.2, 2.2 Hz, 1H), 7.03- 7.07 (m, 1H), 7.10(d, J = 2.2 Hz, 1H), 7.26 (d, J = 8.2 Hz, 1H), 7.51-7.55 (m, 1H),7.58-7.62 (m, 1H), 8.10-8.12 (m, 1H), 8.13- 8.15 (m, 1H), 8.46 (s, 1H)6-[4-(Benzothiophen-3-ylcarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-75)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.04 (s, 3H),2.09 (s, 3H), 3.76 (s, 3H), 4.67 (d, J = 12.2 Hz, 1H), 5.12 (d, J = 12.2Hz, 1H), 5.41 (s, 1H), 6.06 (s, 1H), 6.40 (dd, J = 11.2, 2.4 Hz, 1H),6.54 (td, J = 8.4, 2.4 Hz, 1H), 6.66 (d, J = 8.2 Hz, 1H), 6.83 (d, J =8.2 Hz, 1H), 6.94 (dd, J = 8.2, 2.3 Hz, 1H), 7.03- 7.07 (m, 1H), 7.10(d, J = 2.3 Hz, 1H), 7.26 (d, J = 8.2 Hz, 1H), 7.50-7.54 (m, 1H),7.55-7.59 (m, 1H), 8.16-8.18 (m, 1H), 8.49- 8.52 (m, 1H), 9.03 (s, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-methoxycarbonylbenzoyloxy)phenyl]-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-76)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.75 (s, 3H), 3.85 (s, 3H), 4.64 (d, J = 12.2 Hz, 1H),5.09 (d, J = 12.2 Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.38 (dd, J =11.5, 2.4 Hz, 1H), 6.53 (td, J = 8.3, 2.4 Hz, 1H), 6.62 (d, J = 8.3 Hz,1H), 6.81 (d, J = 8.3 Hz, 1H), 6.89 (dd, J = 8.2, 2.2 Hz, 1H), 7.00 (d,J = 2.2 Hz, 1H), 7.02-7.06 (m, 1H), 7.26 (d, J = 8.2 Hz, 1H), 7.75-7.80(m, 2H), 7.85-7.87 (m, 1H), 7.96-7.99 (m, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-methoxycarbonylbenzoyloxy)phenyl]-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-77)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 3.92 (s, 3H), 4.65 (d, J = 12.2 Hz, 1H),5.10 (d, J = 12.2 Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.38 (dd, J =11.5, 2.4 Hz, 1H), 6.54 (td, J = 8.3, 2.4 Hz, 1H), 6.65 (d, J = 8.3 Hz,1H), 6.82 (d, J = 8.3 Hz, 1H), 6.93 (dd, J = 8.2, 2.2 Hz, 1H), 7.03-7.07(m, 1H), 7.09 (d, J = 2.2 Hz, 1H), 7.25 (d, J = 8.2 Hz, 1H), 8.17 (d, J= 8.6 Hz, 2H), 8.28 (d, J = 8.6 Hz, 2H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(pyrimidin-5-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 1-78)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.07 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.64 (d, J = 12.1 Hz, 1H), 5.09 (d, J = 12.1Hz, 1H), 5.41 (s, 1H), 6.06 (s, 1H), 6.39 (dd, J = 11.3, 2.5 Hz, 1H),6.54 (td, J = 8.3, 2.5 Hz, 1H), 6.65 (d, J = 8.2 Hz, 1H), 6.82 (d, J =8.2 Hz, 1H), 6.95 (dd, J = 8.2, 2.2 Hz, 1H), 7.03-7.06 (m, 1H), 7.13 (d,J = 2.2 Hz, 1H), 7.26 (d, J = 8.2 Hz, 1H), 9.44 (s, 2H), 9.51 (s, 1H)6-[4-(3-Chlorothiophen-2-ylcarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-79)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.15 (s, 3H), 2.02 (s, 3H),2.07 (s, 3H), 3.74 (s, 3H), 4.64 (d, J = 12.3 Hz, 1H), 5.10 (d, J = 12.3Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.37 (dd, J = 11.4, 2.4 Hz, 1H),6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.80 (d, J =8.2 Hz, 1H), 6.88 (dd, J = 8.2, 2.3 Hz, 1H), 7.02-7.06 (m, 1H), 7.04 (d,J = 2.3 Hz, 1H), 7.23 (d, J = 8.2 Hz, 1H), 7.36 (d, J = 5.1 Hz, 1H),8.15 (d, J = 5.1 Hz, 1H)6-[4-(5-Chlorothiophen-2-ylcarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-80)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.02 (s, 3H),2.07 (s, 3H), 3.73 (s, 3H), 4.62 (d, J = 12.1 Hz, 1H), 5.08 (d, J = 12.1Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.37 (dd, J = 11.5, 2.4 Hz, 1H),6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.80 (d, J =8.2 Hz, 1H), 6.88 (dd, J = 8.1, 2.2 Hz, 1H), 7.02-7.06 (m, 1H), 7.04 (d,J = 2.2 Hz, 1H), 7.23 (d, J = 8.1 Hz, 1H), 7.39 (d, J = 4.2 Hz, 1H),7.93 (d, J = 4.2 Hz, 1H)6-[4-(5-Bromothiophen-2-ylcarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-81)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.02 (s, 3H),2.07 (s, 3H), 3.73 (s, 3H), 4.63 (d, J = 12.2 Hz, 1H), 5.09 (d, J = 12.2Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.37 (dd, J = 11.5, 2.4 Hz, 1H),6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.80 (d, J =8.2 Hz, 1H), 6.88 (dd, J = 8.2, 2.2 Hz, 1H), 7.02-7.06 (m, 1H), 7.04 (d,J = 2.2 Hz, 1H), 7.23 (d, J = 8.2 Hz, 1H), 7.48 (d, J = 4.1 Hz, 1H),7.87 (d, J = 4.1 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(5-nitrothiophen-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-82)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.07 (s, 3H), 1.16 (s, 3H), 2.02 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.63 (d, J = 12.1 Hz, 1H), 5.09 (d, J = 12.1Hz, 1H), 5.40 (s, 1H), 6.07 (s, 1H), 6.38 (dd, J = 11.5, 2.5 Hz, 1H),6.54 (td, J = 8.4, 2.5 Hz, 1H), 6.65 (d, J = 8.3 Hz, 1H), 6.81 (d, J =8.3 Hz, 1H), 6.94 (dd, J = 8.3, 2.3 Hz, 1H), 7.02-7.06 (m, 1H), 7.12 (d,J = 2.3 Hz, 1H), 7.25 (d, J = 8.3 Hz, 1H), 8.04 (d, J = 4.4 Hz, 1H),8.24 (d, J = 4.4 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(5-methylthiothiophen-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-83)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.02 (s, 3H),2.07 (s, 3H), 2.67 (s, 3H), 3.73 (s, 3H), 4.63 (d, J = 12.1 Hz, 1H),5.09 (d, J = 12.1 Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.37 (dd, J =11.4, 2.4 Hz, 1H), 6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.2 Hz,1H), 6.80 (d, J = 8.2 Hz, 1H), 6.86 (dd, J = 8.3, 2.4 Hz, 1H), 7.01 (d,J = 2.4 Hz, 1H), 7.02-7.06 (m, 1H), 7.20 (d, J = 4.1 Hz, 1H), 7.22 (d, J= 8.3 Hz, 1H), 7.91 (d, J = 4.1 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(5-phenylthiophen-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 1-84)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.75 (s, 3H), 4.64 (d, J = 12.2 Hz, 1H), 5.10 (d, J = 12.2Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.38 (dd, J = 11.3, 2.4 Hz, 1H),6.54 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.1 Hz, 1H), 6.82 (d, J =8.1 Hz, 1H), 6.90 (dd, J = 8.2, 2.4 Hz, 1H), 7.03-7.06 (m, 1H), 7.05 (d,J = 2.4 Hz, 1H), 7.24 (d, J = 8.2 Hz, 1H), 7.43-7.46 (m, 1H), 7.49-7.52(m, 1H), 7.50 (d, J = 7.6 Hz, 1H), 7.73 (d, J = 4.0 Hz, 1H), 7.82-7.84(m, 1H), 7.83 (d, J = 7.0 Hz, 1H), 8.04 (d, J = 4.0 Hz, 1H)6-[4-(5-Bromofuran-2-ylcarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 1-85)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.02 (s, 3H),2.07 (s, 3H), 3.73 (s, 3H), 4.62 (d, J = 12.1 Hz, 1H), 5.08 (d, J = 12.2Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.37 (dd, J = 11.4, 2.5 Hz, 1H),6.53 (td, J = 8.4, 2.5 Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.80 (d, J =8.2 Hz, 1H), 6.87 (dd, J = 8.3, 2.3 Hz, 1H), 6.97 (d, J = 3.7 Hz, 1H),7.02-7.06 (m, 1H), 7.03 (d, J = 2.3 Hz, 1H), 7.22 (d, J = 8.3 Hz, 1H),7.61 (d, J = 3.7 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(5-nitrofuran-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 1-86)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.07 (s, 3H), 1.16 (s, 3H), 2.02 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.63 (d, J = 12.2 Hz, 1H), 5.09 (d, J = 12.2Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.38 (dd, J = 11.2, 2.5 Hz, 1H),6.54 (td, J = 8.4, 2.5 Hz, 1H), 6.65 (d, J = 8.2 Hz, 1H), 6.81 (d, J =8.2 Hz, 1H), 6.93 (dd, J = 8.2, 2.2 Hz, 1H), 7.02-7.06 (m, 1H), 7.09 (d,J = 2.2 Hz, 1H), 7.26 (d, J = 8.2 Hz, 1H), 7.84 (d, J = 3.9 Hz, 1H),7.89 (d, J = 3.9 Hz, 1H)6-[4-(2-Chloro-6-methylpyridin-4-ylcarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-87)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.07 (s, 3H), 1.17 (s, 3H), 2.02 (s, 3H),2.08 (s, 3H), 2.60 (s, 3H), 3.73 (s, 3H), 4.62 (d, J = 12.0 Hz, 1H),5.09 (d, J = 12.0 Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.38 (dd, J =11.4, 2.3 Hz, 1H), 6.54 (td, J = 8.4, 2.3 Hz, 1H), 6.65 (d, J = 8.3 Hz,1H), 6.81 (d, J = 8.3 Hz, 1H), 6.94 (dd, J = 8.3, 2.3 Hz, 1H), 7.02-7.07 (m, 1H), 7.11 (d, J = 2.3 Hz, 1H), 7.26 (d, J = 8.3 Hz, 1H), 7.88(d, J = 1.0 Hz, 1H), 7.93 (d, J = 1.0 Hz, 1H)6-[4-(3,5-Dichloropyridin-4-ylcarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-88)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.02 (s, 3H),2.07 (s, 3H), 3.78 (s, 3H), 4.63 (d, J = 12.1 Hz, 1H), 5.09 (d, J = 12.1Hz, 1H), 5.41 (s, 1H), 6.08 (s, 1H), 6.40 (dd, J = 11.4, 2.4 Hz, 1H),6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.66 (d, J = 8.3 Hz, 1H), 6.81 (d, J =8.3 Hz, 1H), 6.93-6.95 (m, 1H), 6.93 (d, J = 2.2 Hz, 1H), 7.02-7.06 (m,1H), 7.31 (d, J = 8.5 Hz, 1H), 8.91 (s, 2H)6-[4-(3-Chloropyridin-4-ylcarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-89)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.07 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.63 (d, J = 12.1 Hz, 1H), 5.09 (d, J = 12.1Hz, 1H), 5.41 (s, 1H), 6.06 (s, 1H), 6.38 (dd, J = 11.4, 2.4 Hz, 1H),6.54 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.2 Hz, 1H), 6.81 (d, J =8.2 Hz, 1H), 6.95 (dd, J = 8.3, 2.2 Hz, 1H), 7.03- 7.07 (m, 1H), 7.13(d, J = 2.2 Hz, 1H), 7.26 (d, J = 8.3 Hz, 1H), 8.03 (dd, J = 5.0, 1.8Hz, 1H), 8.10 (dd, J = 1.8, 0.7 Hz, 1H), 8.72 (dd, J = 5.0, 0.7 Hz, 1H)6-[4-(2-Chloropyridin-4-ylcarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-90)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.75 (s, 3H), 4.64 (d, J = 12.0 Hz, 1H), 5.10 (d, J = 12.0Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.38 (dd, J = 11.5, 2.4 Hz, 1H),6.53 (td, J = 8.5, 2.4 Hz, 1H), 6.65 (d, J = 8.2 Hz, 1H), 6.82 (d, J =8.2 Hz, 1H), 6.95 (dd, J = 8.2, 2.2 Hz, 1H), 7.02- 7.06 (m, 1H), 7.11(d, J = 2.2 Hz, 1H), 7.27 (d, J = 8.2 Hz, 1H), 8.06 (d, J = 4.9 Hz, 1H),8.79 (d, J = 4.9 Hz, 1H), 8.91 (s, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[4-(3-fluoropyridin-4-ylcarbonyloxy)-2-methoxyphenyl]-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-91)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.64 (d, J = 12.2 Hz, 1H), 5.10 (d, J = 12.2Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.38 (dd, J = 11.5, 2.4 Hz, 1H),6.53 (td, J = 8.3, 2.4 Hz, 1H), 6.65 (d, J = 8.2 Hz, 1H), 6.82 (d, J =8.2 Hz, 1H), 6.94 (dd, J = 8.2, 2.3 Hz, 1H), 7.02- 7.06 (m, 1H), 7.11(d, J = 2.3 Hz, 1H), 7.26 (d, J = 8.2 Hz, 1H), 8.03-8.05 (m, 1H), 8.70(d, J = 4.9 Hz, 1H), 8.88 (d, J = 2.2 Hz, 1H)6-(4-Butyryloxy-2-methoxyphenyl)-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-92)  

¹H-NMR (500 MHz, DMSO-D₆) δ 0.90 (s, 3H), 0.98 (t, J = 7.5 Hz, 3H), 1.18(s, 3H), 1.63-1.69 (m, 2H), 2.12 (s, 3H), 2.18 (s, 3H), 2.56 (t, J = 7.2Hz, 2H), 3.73 (s, 3H), 4.77 (d, J = 12.5 Hz, 1H), 5.30 (d, J = 12.5 Hz,1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.62 (d, J = 8.2 Hz, 1H), 6.75 (dd, J =8.2, 2.1 Hz, 1H), 6.79 (d, J = 8.2 Hz, 1H), 6.85 (d, J = 2.1 Hz, 1H),7.14 (d, J = 2.1 Hz, 1H), 7.27 (d, J = 8.2 Hz, 1H), 7.33 (d, J = 8.1 Hz,1H), 7.63 (dd, J = 8.1, 2.1 Hz, 1H)6-[2-Methoxy-4-(2-methoxybenzoyloxy)phenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-93)  

¹H-NMR (500 MHz, DMSO-D₆) δ 0.90 (s, 3H), 1.19 (s, 3H), 2.13 (s, 3H),2.19 (s, 3H), 3.76 (s, 3H), 3.88 (s, 3H), 4.81 (d, J = 12.7 Hz, 1H),5.34 (d, J = 12.7 Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.63 (d, J = 8.2Hz, 1H), 6.82 (d, J = 8.2 Hz, 1H), 6.88 (dd, J = 8.2, 2.3 Hz, 1H), 6.99(d, J = 2.3 Hz, 1H), 7.11 (t, J = 7.5 Hz, 1H), 7.17 (d, J = 2.0 Hz, 1H),7.24 (d, J = 8.6 Hz, 1H), 7.32 (d, J = 8.2 Hz, 1H), 7.34 (d, J = 7.9 Hz,1H), 7.63-7.66 (m, 2H), 7.93 (dd, J = 7.9, 2.0 Hz, 1H)6-[2-Methoxy-4-(pyridin-3-ylcarbonyloxy)phenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-94)  

¹H-NMR (400 MHz, DMSO-D₆) δ 0.91 (s, 3H), 1.19 (s, 3H), 2.14 (s, 3H),2.19 (s, 3H), 3.76 (s, 3H), 4.81 (d, J = 12.5 Hz, 1H), 5.33 (d, J = 12.5Hz, 1H), 5.41 (s, 1H), 6.07 (s, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.83 (d,J = 8.2 Hz, 1H), 6.97 (dd, J = 8.3, 2.2 Hz, 1H), 7.11 (d, J = 2.2 Hz,1H), 7.18 (d, J = 2.2 Hz, 1H), 7.34 (d, J = 8.3 Hz, 1H), 7.34 (d, J =8.3 Hz, 1H), 7.63-7.68 (m, 2H), 8.48 (dt, J = 8.1, 2.0 Hz, 1H), 8.91(dd, J = 4.8, 2.0 Hz, 1H), 9.28 (dd, J = 2.0, 0.7 Hz, 1H)6-[4-(Furan-2-ylcarbonyloxy)-2-methoxyphenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline (CompoundNo. 1-95)  

¹H-NMR (500 MHz, DMSO-D₆) δ 0.91 (s, 3H), 1.19 (s, 3H), 2.13 (s, 3H),2.19 (s, 3H), 3.75 (s, 3H), 4.80 (d, J = 12.7 Hz, 1H), 5.32 (d, J = 12.7Hz, 1H), 5.41 (s, 1H), 6.06 (s, 1H), 6.63 (d, J = 8.6 Hz, 1H), 6.81 (dd,J = 3.4, 1.8 Hz, 1H), 6.82 (d, J = 8.6 Hz, 1H), 6.90 (dd, J = 8.2, 2.2Hz, 1H), 7.03 (d, J = 2.2 Hz, 1H), 7.17 (d, J = 2.1 Hz, 1H), 7.32 (d, J= 8.2 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 7.57 (dd, J = 3.4, 0.8 Hz, 1H),7.64 (dd, J = 8.2, 2.1 Hz, 1H), 8.11 (dd, J = 1.8, 0.8 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(5-methoxyfuran-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-96)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 4.64 (d, J = 12.2 Hz, 1H), 5.10 (d, J = 12.2Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.38 (dd, J = 11.5, 2.4 Hz, 1H),6.53 (td, J = 8.3, 2.4 Hz, 1H), 6.65 (d, J = 8.2 Hz, 1H), 6.82 (d, J =8.2 Hz, 1H), 6.94 (dd, J = 8.2, 2.3 Hz, 1H), 7.02-7.06 (m, 1H), 7.11 (d,J = 2.3 Hz, 1H), 7.26 (d, J = 8.2 Hz, 1H), 8.03-8.05 (m, 1H), 8.70 (d, J= 4.9 Hz, 1H), 8.88 (d, J = 2.2 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(5-methylpyridin-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-97)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.16 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 2.43 (s, 3H), 3.74 (s, 3H), 4.64 (d, J = 12.5 Hz, 1H),5.10 (d, J = 12.5 Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.36 (dd, J =11.5, 2.4 Hz, 1H), 6.54 (td, J = 8.3, 2.4 Hz, 1H), 6.65 (d, J = 8.2 Hz,1H), 6.82 (d, J = 8.2 Hz, 1H), 6.92 (dd, J = 8.2, 2.2 Hz, 1H), 7.03-7.07(m, 1H), 7.09 (d, J = 2.2 Hz, 1H), 7.25 (d, J = 8.2 Hz, 1H), 8.31 (s,1H), 8.75 (s, 1H), 9.08 (s, 1H)6-[4-(2-Chlorobenzoyloxy)-2-methoxyphenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-98)  

¹H-NMR (400 MHz, DMSO-d₃) δ 1.04 (s, 3H), 1.19 (s, 3H), 2.15 (s, 3H),3.72 (s, 3H), 3.83 (s, 3H), 4.69 (d, J = 12.0 Hz, 1H), 5.28 (d, J = 12.0Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.79 (d,J = 8.2 Hz, 1H), 6.84 (dd, J = 8.2 , 2.2 Hz, 1H), 7.01 (d, J = 2.2 Hz,1H), 7.09 (d, J = 9.0 Hz, 1H), 7.22 (d, J = 8.2 Hz, 1H), 7.34 (d, J =2.7 Hz, 1H), 7.54-7.58 (m, 1H), 7.67-7.69 (m, 2H), 7.82 (dd, J = 9.0,2.7 Hz, 1H), 8.09 (ddd, J = 7.7, 1.2, 0.7 Hz, 1H)5-(2-Methoxy-5-nitrophenoxymethyl)-6-[2-methoxy-4-(pyridin-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-99)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.19 (s, 3H), 2.15 (s, 3H),3.70 (s, 3H), 3.83 (s, 3H), 4.69 (d, J = 11.9 Hz, 1H), 5.28 (d, J = 11.9Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.79 (d,J = 8.2 Hz, 1H), 6.85 (dd, J = 8.3, 2.3 Hz, 1H), 7.05 (d, J = 2.3 Hz,1H), 7.09 (d, J = 9.1 Hz, 1H), 7.21 (d, J = 8.3 Hz, 1H), 7.34 (d, J =2.7 Hz, 1H), 7.66 (ddd, J = 8.1, 4.9, 1.0 Hz, 1H), 7.82 (dd, J = 9.1,2.7 Hz, 1H), 8.46 (dt, J = 8.1, 1.9 Hz, 1H), 8.90 (dd, J = 4.9, 1.9 Hz,1H), 9.25 (dd, J = 1.9, 1.0 Hz, 1H)5-(2-Methoxy-5-nitrophenoxymethyl)-6-[2-methoxy-4-(pyridin-4-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-100)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.19 (s, 3H), 2.15 (s, 3H),3.70 (s, 3H), 3.83 (s, 3H), 4.68 (d, J = 11.9 Hz, 1H), 5.27 (d, J = 11.9Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.64 (d, J = 8.1 Hz, 1H), 6.79 (d,J = 8.1 Hz, 1H), 6.85 (dd, J = 8.2, 2.4 Hz, 1H), 7.05 (d, J = 2.4 Hz,1H), 7.09 (d, J = 9.1 Hz, 1H), 7.22 (d, J = 8.2 Hz, 1H), 7.34 (d, J =2.7 Hz, 1H), 7.82 (dd, J = 9.1, 2.7 Hz, 1H), 8.00 (d, J = 6.0 Hz, 2H),8.89 (d, J = 6.0 Hz, 2H)6-[2-Methoxy-4-(2-methylpyridin-3-ylcarbonyloxy)phenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-101)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.04 (s, 3H), 1.19 (s, 3H), 2.15 (s, 3H),2.78 (s, 3H), 3.71 (s, 3H), 3.83 (s, 3H), 4.69 (d, J = 12.3 Hz, 1H),5.28 (d, J = 12.3 Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.64 (d, J = 8.3Hz, 1H), 6.79 (d, J = 8.3 Hz, 1H), 6.84 (dd, J = 8.3, 2.2 Hz, 1H), 7.04(d, J = 2.2 Hz, 1H), 7.09 (d, J = 9.0 Hz, 1H), 7.21 (d, J = 8.3 Hz, 1H),7.33 (d, J = 2.8 Hz, 1H), 7.47 (dd, J = 8.1, 4.9 Hz, 1H), 7.82 (dd, J =9.0, 2.8 Hz, 1H), 8.42 (dd, J = 8.1, 1.8 Hz, 1H), 8.71 (dd, J = 4.9, 1.8Hz, 1H) 6-[2-Methoxy-4-(2-methoxybenzoyloxy)phenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-102)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.04 (s, 3H), 1.19 (s, 3H), 2.15 (s, 3H),3.71 (s, 3H), 3.83 (s, 3H), 3.87 (s, 3H), 4.69 (d, J = 12.2 Hz, 1H),5.28 (d, J = 12.2 Hz, 1H), 5.40 (s, 1H), 6.02 (s, 1H), 6.63 (d, J = 8.2Hz, 1H), 6.77 (dd, J = 7.9, 2.2 Hz, 1H), 6.78 (d, J = 8.2 Hz, 1H), 6.93(d, J = 2.2 Hz, 1H), 7.09 (d, J = 9.1 Hz, 1H), 7.10 (d, J = 8.1 Hz, 1H),7.19 (d, J = 7.9 Hz, 1H), 7.23 (d, J = 8.1 Hz, 1H), 7.33 (d, J = 2.6 Hz,1H), 7.64 (ddd, J = 8.1, 7.3, 1.7 Hz, 1H), 7.82 (dd, J = 9.1, 2.6 Hz,1H), 7.90 (dd, J = 7.3, 1.7 Hz, 1H)6-[4-(Furan-2-ylcarbonyloxy)-2-methoxyphenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-103)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.19 (s, 3H), 2.15 (s, 3H),3.69 (s, 3H), 3.82 (s, 3H), 4.67 (d, J = 11.9 Hz, 1H), 5.27 (d, J = 11.9Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.63 (d, J = 8.2 Hz, 1H), 6.78 (d,J = 8.2 Hz, 1H), 6.79 (dd, J = 8.2, 2.2 Hz, 1H), 6.80 (dd, J = 3.5, 1.8Hz, 1H), 6.97 (d, J = 2.2 Hz, 1H), 7.09 (d, J = 9.2 Hz, 1H), 7.19 (d, J= 8.2 Hz, 1H), 7.33 (d, J = 2.7 Hz, 1H), 7.55 (dd, J = 3.5, 0.9 Hz, 1H),7.82 (dd, J = 9.2, 2.7 Hz, 1H), 8.10 (dd, J = 1.8, 0.9 Hz, 1H)6-(4-Isopropylcarbonyloxy-2-methoxyphenyl)-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-104)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.03 (s, 3H), 1.18 (s, 3H), 1.23 (d, J = 7.0Hz, 6H), 2.14 (s, 3H), 2.76-2.82 (m, 1H), 3.68 (s, 3H), 3.81 (s, 3H),4.65 (d, J = 12.1 Hz, 1H), 5.25 (d, J = 12.1 Hz, 1H), 5.39 (s, 1H), 6.01(s, 1H), 6.62 (d, J = 8.2 Hz, 1H), 6.63 (dd, J = 7.9, 2.1 Hz, 1H), 6.75(d, J = 8.2 Hz, 1H), 6.78 (d, J = 2.1 Hz, 1H), 7.08 (d, J = 9.2 Hz, 1H),7.14 (d, J = 7.9 Hz, 1H), 7.31 (d, J = 2.7 Hz, 1H), 7.81 (dd, J = 9.2,2.7 Hz, 1H) 6-[2-Methoxy-4-(3-methoxycarbonylbenzoyloxy)phenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-105)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.19 (s, 3H), 2.15 (s, 3H),3.71 (s, 3H), 3.83 (s, 3H), 3.92 (s, 3H), 4.69 (d, J = 12.0 Hz, 1H),5.28 (d, J = 12.0 Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.64 (d, J = 8.3Hz, 1H), 6.79 (d, J = 8.3 Hz, 1H), 6.85 (dd, J = 8.2, 2.2 Hz, 1H), 7.04(d, J = 2.2 Hz, 1H), 7.09 (d, J = 9.2 Hz, 1H), 7.22 (d, J = 8.2 Hz, 1H),7.34 (d, J = 2.7 Hz, 1H), 7.79 (t, J = 8.1 Hz, 1H), 7.82 (dd, J = 9.2,2.7 Hz, 1H), 8.31 (d, J = 8.1 Hz, 1H), 8.38 (d, J = 8.1 Hz, 8.64 (s, 1H)6-[4-(3-Chlorobenzoyloxy)-2-methoxyphenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-106)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.19 (s, 3H), 2.15 (s, 3H),3.70 (s, 3H), 3.83 (s, 3H), 4.68 (d, J = 11.9 Hz, 1H), 5.28 (d, J = 11.9Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.63 (d, J = 8.2 Hz, 1H), 6.79 (d,J = 8.2 Hz, 1H), 6.84 (dd, J = 8.2, 2.2 Hz, 1H), 7.03 (d, J = 2.2 Hz,1H), 7.09 (d, J = 9.3 Hz, 1H), 7.20 (d, J = 8.2 Hz, 1H), 7.34 (d, J =2.6 Hz, 1H), 7.66 (t, J = 7.4 Hz, 1H), 7.82 (dd, J = 9.3, 2.6 Hz, 1H),7.83-7.85 (m, 1H), 8.06-8.11 (m, 2H)6-[4-(4-Chlorobenzoyloxy)-2-methoxyphenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-107)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.19 (s, 3H), 2.15 (s, 3H),3.70 (s, 3H), 3.83 (s, 3H), 4.69 (d, J = 11.8 Hz, 1H), 5.28 (d, J = 11.8Hz, 1H), 5.40 (s, 1H), 6.03 (s, 1H), 6.63 (d, J = 8.1 Hz, 1H), 6.79 (d,J = 8.1 Hz, 1H), 6.82 (dd, J = 7.9, 2.1 Hz, 1H), 7.01 (d, J = 2.1 Hz,1H), 7.09 (d, J = 9.1 Hz, 1H), 7.20 (d, J = 7.9 Hz, 1H), 7.33 (d, J =2.7 Hz, 1H), 7.69 (d, J = 8.6 Hz, 2H), 7.82 (dd, J = 9.1, 2.7 Hz, 1H),8.12 (d, J = 8.6 Hz, 2H)6-(4-Butyryloxy-2-methoxyphenyl)-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-108)  

¹H-NMR (500 MHz, DMSO-d₆) δ 0.97 (t, J = 7.5 Hz, 3H), 1.03 (s, 3H), 1.18(s, 3H), 1.65 (qt, J = 7.5, 7.4 Hz, 2H), 2.14 (s, 3H), 2.53 (t, J = 7.4Hz, 2H), 3.67 (s, 3H), 3.81 (s, 3H), 4.65 (d, J = 11.9 Hz, 1H), 5.25 (d,J = 11.9 Hz, 1H), 5.39 (s, 1H), 6.01 (s, 1H), 6.62 (d, J = 8.2 Hz, 1H),6.64 (dd, J = 8.3, 2.4 Hz, 1H), 6.75 (d, J = 8.2 Hz, 1H), 6.79 (d, J =2.4 Hz, 1H), 7.08 (d, J = 9.1 Hz, 1H), 7.14 (d, J = 8.3 Hz, 1H), 7.31(d, 2.7 Hz, 1H), 7.81 (dd, J = 9.1, 2.7 Hz, 1H)6-(4-Benzoyloxy-2-methoxyphenyl)-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-109)  

¹H-NMR (400 MHz, CDCl₃) δ 1.04 (s, 3H), 1.27 (s, 3H), 2.28 (s, 3H), 3.77(s, 3H), 3.84 (s, 4H), 4.88 (d, J = 12.3 Hz, 1H), 5.40 (d, J = 12.3 Hz,1H), 5.47 (s, 1H), 6.57 (d, J = 8.1 Hz, 1H), 6.78 (d, J = 8.8 Hz, 1H),6.81 (d, J = 2.2 Hz, 1H), 6.84 (d, J = 8.1, 2.2 Hz, 1H), 6.90 (d, J =8.1 Hz, 1H), 7.32 (d, J = 2.7 Hz, 1H), 7.32 (d, J = 8.1 Hz, 1H), 7.52(t, J = 7.4 Hz, 2H), 7.65 (t, J = 7.4 Hz, 1H), 7.79 (dd, J = 8.8, 2.7Hz, 1H), 8.21 (d, J = 7.4 Hz, 2H)6-[2-Methoxy-4-(2-methylbenzoyloxy)phenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-110)  

¹H-NMR (400 MHz, CDCl₃) δ 1.02 (s, 3H), 1.27 (s, 3H), 2.28 (s, 3H), 2.69(s, 3H), 3.78 (s, 3H), 3.85 (s, 4H), 4.88 (d, J = 12.5 Hz, 1H), 5.40 (d,J = 12.5 Hz, 1H), 5.46 (s, 1H), 6.57 (d, J = 8.1 Hz, 1H), 6.78 (d, J =8.9 Hz, 1H), 6.79 (d, J = 2.1 Hz, 1H), 6.83 (dd, J = 8.1, 2.1 Hz, 1H),6.90 (d, J = 8.1 Hz, 1H), 7.31-7.35 (m, 3H), 7.31 (d, J = 2.7 Hz, 1H),7.47-7.51 (m, 1H), 7.78 (dd, J = 8.9, 2.7 Hz, 1H), 8.17 (dd, J = 8.5,1.5 Hz, 1H) 6-[4-(2-Chlorobenzoyloxy)-2-methoxyphenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl,1-2-dihydroquinoline (Compound No.1-111)  

¹H-NMR (400 MHz, DMSO-d₆) δ 0.91 (s, 3H), 1.19 (s, 3H), 2.14 (s, 3H),2.19 (s, 3H), 3.77 (s, 3H), 4.81 (d, J = 12.9 Hz, 1H), 5.34 (d, J = 12.9Hz, 1H), 5.41 (s, 1H), 6.06 (s, 1H), 6.64 (d, J = 8.3 Hz, 1H), 6.83 (d,J = 8.3 Hz, 1H), 6.95 (dd, J = 8.2, 2.2 Hz, 1H), 7.08 (d, J = 2.2 Hz,1H), 7.18 (d, J = 2.2 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 7.35 (d, J =8.2 Hz, 1H), 7.55-7.59 (m, 1H), 7.64 (d, J = 8.2, 2.2 Hz, 1H), 7.68-7.69(m, 2H), 8.11 (d, J = 7.6 Hz, 1H)6-[2-Methoxy-4-(3-methylbenzoyloxy)phenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-112)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.19 (s, 3H), 2.15 (s, 3H),2.42 (s, 3H), 3.70 (s, 3H), 3.83 (s, 3H), 4.69 (d, J = 12.1 Hz, 1H),5.28 (d, J = 12.1 Hz, 1H), 5.40 (s, 1H), 6.03 (s, 1H), 6.64 (d, J = 8.2Hz, 1H), 6.79 (d, J = 8.2 Hz, 1H), 6.80 (dd, J = 7.9, 2.2 Hz, 1H), 6.98(d, J = 2.2 Hz, 1H), 7.09 (d, J = 9.1 Hz, 1H), 7.20 (d, J = 7.9 Hz, 1H),7.34 (d, J = 2.5 Hz, 1H), 7.49 (t, J = 7.7 Hz, 1H), 7.56 (d, J = 7.7 Hz,1H), 7.82 (dd, J = 9.1, 2.5 Hz, 1H), 7.92 (d, J = 7.7 Hz, 1H), 7.95 (s,1H) 6-[2-Methoxy-4-(4-methylbenzoyloxy)phenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-113)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.19 (s, 3H), 2.15 (s, 3H),2.43 (s, 3H), 3.70 (s, 3H), 3.83 (s, 3H), 4.69 (d, J = 11.9 Hz, 1H),5.28 (d, J = 11.9 Hz, 1H), 5.40 (s, 1H), 6.03 (s, 1H), 6.63 (d, J = 8.2Hz, 1H), 6.79 (d, J = 8.2 Hz, 1H), 6.80 (dd, J = 8.0, 2.2 Hz, 1H), 6.97(d, J = 2.2 Hz, 1H), 7.09 (d, J = 9.1 Hz, 1H), 7.19 (d, J = 8.0 Hz, 1H),7.34 (d, J = 2.7 Hz, 1H), 7.42 (d, J = 8.2 Hz, 2H), 7.82 (dd, J = 9.1,2.7 Hz, 1H), 8.01 (d, J = 8.2 Hz, 2H)5-(2-Methoxy-5-nitrophenoxymethyl)-6-[2-methoxy-4-(thiophen-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-114)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.04 (s, 3H), 1.19 (s, 3H), 2.15 (s, 3H),3.70 (s, 3H), 3.83 (s, 3H), 4.68 (d, J = 12.1 Hz, 1H), 5.27 (d, J = 12.1Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.63 (d, J = 8.3 Hz, 1H), 6.78 (d,J = 8.3 Hz, 1H), 6.80 (dd, J = 8.2, 2.2 Hz, 1H), 6.98 (d, J = 2.2 Hz,1H), 7.09 (d, J = 9.2 Hz, 1H), 7.19 (d, J = 8.2 Hz, 1H), 7.31 (dd, J =5.0, 3.8 Hz, 1H), 7.34 (d, J = 2.7 Hz, 1H), 7.82 (dd, J = 9.2, 2.7 Hz,1H), 8.01 (dd, J = 3.8, 1.2 Hz, 1H), 8.10 (dd, J = 5.0, 1.2 Hz, 1H)5-(2-Methoxy-5-nitrophenoxymethyl)-6-[2-methoxy-4-(thiophen-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-115)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.04 (s, 3H), 1.19 (s, 3H), 2.15 (s, 3H),3.69 (s, 3H), 3.83 (s, 3H), 4.68 (d, J = 11.9 Hz, 1H), 5.27 (d, J = 11.9Hz, 1H), 5.40 (s, 1H), 6.03 (s, 1H), 6.63 (d, J = 8.2 Hz, 1H), 6.78 (d,J = 8.2 Hz, 2H), 6.96 (d, J = 2.1 Hz, 1H), 7.09 (d, J = 9.1 Hz, 1H),7.19 (d, J = 8.2 Hz, 1H), 7.33 (d, J = 2.7 Hz, 1H), 7.60 (dd, J = 5.1,1.2 Hz, 1H), 7.75 (dd, J = 5.1, 3.1 Hz, 1H), 7.82 (dd, J = 9.1, 2.7 Hz,1H), 8.58 (dd, J = 3.1, 1.2 Hz, 1H)6-[4-(2-Fluorobenzoyloxy)-2-methoxyphenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-116)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.04 (s, 3H), 1.19 (s, 3H), 2.15 (s, 3H),3.71 (s, 3H), 3.83 (s, 3H), 4.69 (d, J = 11.9 Hz, 1H), 5.28 (d, J = 11.9Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.63 (d, J = 8.2 Hz, 1H), 6.79 (d,J = 8.2 Hz, 2H), 6.82 (dd, J = 8.2, 2.3 Hz, 1H), 7.01 (d, J = 2.3 Hz,1H), 7.09 (d, J = 9.0 Hz, 1H), 7.21 (d, J = 8.2 Hz, 1H), 7.34 (d, J =2.7 Hz, 1H), 7.40- 7.46 (m, 2H), 7.75-7.81 (m, 1H), 7.82 (dd, J = 9.0,2.7 Hz, 1H), 8.09 (t, J = 7.7 Hz, 1H)6-[4-(4-Fluorobenzoyloxy)-2-methoxyphenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-117)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.19 (s, 3H), 2.15 (s, 3H),3.70 (s, 3H), 3.83 (s, 3H), 4.69 (d, J = 11.9 Hz, 1H), 5.28 (d, J = 11.9Hz, 1H), 5.40 (s, 1H), 6.03 (s, 1H), 6.63 (d, J = 8.2 Hz, 1H), 6.79 (d,J = 8.2 Hz, 1H), 6.81 (dd, J = 8.1, 2.3 Hz, 1H), 7.00 (d, J = 2.3 Hz,1H), 7.09 (d, J = 9.1 Hz, 1H), 7.20 (d, J = 8.1 Hz, 1H), 7.33 (d, J =2.7 Hz, 1H), 7.45 (t, J = 9.1 Hz, 2H), 7.82 (dd, J = 9.1, 2.7 Hz, 1H),8.19 (dd, J = 9.1, 5.5 Hz, 2H)6-[2-Methoxy-4-(2-nitrobenzoyloxy)phenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-118)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.04 (s, 3H), 1.19 (s, 3H), 2.15 (s, 3H),3.71 (s, 3H), 3.82 (s, 3H), 4.69 (d, J = 12.1 Hz, 1H), 5.27 (d, J = 12.1Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.63 (d, J = 8.3 Hz, 1H), 6.78 (d,J = 8.3 Hz, 1H), 6.81 (dd, J = 8.2, 2.2 Hz, 1H), 6.97 (d, J = 2.2 Hz,1H), 7.08 (d, J = 9.0 Hz, 1H), 7.23 (d, J = 8.2 Hz, 1H), 7.33 (d, J =2.7 Hz, 1H), 7.81 (dd, J = 9.0, 2.7 Hz, 1H), 7.91 (td, J = 7.7, 1.6 Hz,1H), 7.96 (td, J = 7.7, 1.3 Hz, 1H), 8.10 (dd, J = 7.7, 1.6 Hz, 1H),8.19 (dd, J = 7.7, 1.3 Hz, 1H)6-[2-Methoxy-4-(4-methoxybenzoyloxy)phenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 1-119)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.04 (s, 3H), 1.19 (s, 3H), 2.15 (s, 3H),3.70 (s, 3H), 3.83 (s, 3H), 3.88 (s, 3H), 4.69 (d, J = 11.8 Hz, 1H),5.28 (d, J = 11.8 Hz, 1H), 5.40 (s, 1H), 6.02 (s, 1H), 6.63 (d, J = 8.2Hz, 1H), 6.78 (dd, J = 8.0, 2.2 Hz, 1H), 6.78 (d, J = 8.2 Hz, 1H), 6.96(d, J = 2.2 Hz, 1H), 7.09 (d, J = 9.1 Hz, 1H), 7.13 (d, J = 8.9 Hz, 2H),7.19 (d, J = 8.0 Hz, 1H), 7.33 (d, J = 2.5 Hz, 1H), 7.82 (dd, J = 9.1,2.5 Hz, 1H), 8.07 (d, J = 8.9 Hz, 2H)6-[2-Methoxy-4-(thiophen-3-ylcarbonyloxy)phenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-120)  

¹H-NMR (400 MHz, DMSO-d₆) δ 0.91 (s, 3H), 1.19 (s, 3H), 2.13 (s, 3H),2.19 (s, 3H), 3.75 (s, 3H), 4.80 (d, J = 12.7 Hz, 1H), 5.33 (d, J = 12.7Hz, 1H), 5.41 (s, 1H), 6.05 (s, 1H), 6.63 (d, J = 8.2 Hz, 1H), 6.82 (d,J = 8.2 Hz, 1H), 6.89 (dd, J = 8.3, 2.2 Hz, 1H), 7.02 (d, J = 2.2 Hz,1H), 7.17 (d, J = 2.1 Hz, 1H), 7.32 (d, J = 8.3 Hz, 1H), 7.34 (d, J =8.1 Hz, 1H), 7.62 (dd, J = 5.1, 1.3 Hz, 1H), 7.64 (dd, J = 8.1, 2.1 Hz,1H), 7.75 (dd, J = 5.1, 2.9 Hz, 1H), 8.61 (dd, J = 2.9, 1.3 Hz, 1H)6-[4-(Furan-3-ylcarbonyloxy)-2-methoxyphenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-121)  

¹H-NMR (400 MHz, DMSO-d₆) δ 0.91 (s, 3H), 1.18 (s, 3H), 2.13 (s, 3H),2.19 (s, 3H), 3.74 (s, 3H), 4.79 (d, J = 12.2 Hz, 1H), 5.32 (d, J = 12.2Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.63 (d, J = 8.3 Hz, 1H), 6.82 (d,J = 8.3 Hz, 1H), 6.87 (dd, J = 8.1, 2.4 Hz, 1H), 6.94 (dd, J = 1.7, 0.7Hz, 1H), 6.99 (d, J = 2.4 Hz, 1H), 7.17 (d, J = 2.3 Hz, 1H), 7.31 (d, J= 8.1 Hz, 1H), 7.33 (d, J = 8.2 Hz, 1H), 7.64 (dd, J = 8.2, 2.3 Hz, 1H),7.92 (t, J = 1.7 Hz, 1H), 8.64 (dd, J = 1.7, 0.7 Hz, 1H)6-[2-Methoxy-4-(2-methylpyridin-3-ylcarbonyloxy)phenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2- dihydroquinoline(Compound No. 1-122)  

¹H-NMR (400 MHz, DMSO-d₆) δ 0.91 (s, 3H), 1.19 (s, 3H), 2.14 (s, 3H),2.19 (s, 3H), 2.80 (s, 3H), 3.76 (s, 3H), 4.81 (d, J = 12.7 Hz, 1H),5.34 (d, J = 12.7 Hz, 1H), 5.41 (s, 1H), 6.06 (s, 1H), 6.64 (d, J = 8.3Hz, 1H), 6.83 (d, J = 8.3 Hz, 1H), 6.95 (dd, J = 8.1, 2.3 Hz, 1H), 7.10(d, J = 2.3 Hz, 1H), 7.18 (d, J = 2.1 Hz, 1H), 7.34 (d, J = 8.1 Hz, 2H),7.47 (dd, J = 8.0, 4.9 Hz, 1H), 7.64 (dd, J = 8.1, 2.1 Hz, 1H), 8.45(dd, J = 8.0, 1.7 Hz, 1H), 8.72 (dd, J = 4.9, 1.7 Hz, 1H)6-[2-Methoxy-4-(3-methylfuran-2-ylcarbonyloxy)phenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 1-123)  

¹H-NMR (500 MHz, DMSO-d₆) δ 0.90 (s, 3H), 1.19 (s, 3H), 2.13 (s, 3H),2.19 (s, 3H), 2.38 (s, 3H), 3.75 (s, 3H), 4.81 (d, J = 12.5 Hz, 1H),5.33 (d, J = 12.5 Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.63 (d, J = 8.1Hz, 1H), 6.70 (d, J = 1.7 Hz, 1H), 6.81 (d, J = 8.1 Hz, 1H), 6.89 (dd, J= 8.2, 2.4 Hz, 1H), 7.01 (d, J = 2.4 Hz, 1H), 7.17 (d, J = 2.3 Hz, 1H),7.31 (d, J = 8.2 Hz, 1H), 7.33 (d, J = 8.2 Hz, 1H), 7.64 (dd, J = 8.2,2.3 Hz, 1H), 7.95 (d, J = 1.7 Hz, 1H)6-[2-Methoxy-4-(pyridin-4-ylcarbonyloxy)phenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.1-124)  

¹H-NMR (500 MHz, DMSO-d₆) δ 0.91 (s, 3H), 1.19 (s, 3H), 2.13 (s, 3H),2.19 (s, 3H), 3.75 (s, 3H), 4.81 (d, J = 12.7 Hz, 1H), 5.33 (d, J = 12.7Hz, 1H), 5.41 (s, 1H), 6.06 (s, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.83 (d,J = 8.2 Hz, 1H), 6.97 (dd, J = 8.2, 2.1 Hz, 1H), 7.11 (d, J = 2.1 Hz,1H), 7.18 (d, J = 2.2 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 7.34 (d, J =8.2 Hz, 1H), 7.65 (dd, J = 8.2, 2.2 Hz, 1H), 8.02 (d, J = 6.1 Hz, 2H),8.90 (d, J = 6.1 Hz, 2H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-methoxypyridin-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-125)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.03 (s, 3H),2.08 (s, 3H), 3.74 (s, 3H), 3.98 (s, 3H), 4.64 (d, J = 12.1 Hz, 1H),5.10 (d, J = 12.1 Hz, 1H), 5.40 (s, 1H), 6.04 (s, 1H), 6.37 (dd, J =11.5, 2.4 Hz, 1H), 6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.65 (d, J = 8.3 Hz,1H), 6.81 (d, J = 8.3 Hz, 1H), 6.86 (dd, J = 8.1, 2.3 Hz, 1H), 7.01 (d,J = 2.3 Hz, 1H), 7.02-7.06 (m, 1H), 7.20 (dd, J = 7.6, 4.9 Hz, 1H), 7.23(d, J = 8.1 Hz, 1H), 8.41 (dd, J = 7.6, 2.0 Hz, 1H), 8.48 (dd, J = 4.9,2.0 Hz, 1H)

Example 26-(5-Acetoxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 2)

5-(5-Fluoro-2-methylphenoxymethyl)-6-(5-hydroxy-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Reference Compound No. 3-2, 62.5 mg, 0.14 mmol) and triethylamine (154μL, 1.11 mmol) were dissolved in anhydrous methylene dichloride (1 mL),acetic anhydride (52 μL, 0.55 mmol) was added thereto, and then themixture was stirred at room temperature for 1.5 hours. Chloroform (10mL) was added to the reaction mixture, the mixture was washed with water(10 mL) and saturated brine (300 mL) successively, dried over anhydrousmagnesium sulfate, and then the solvent was removed under reducedpressure. The residue was purified by silica gel column chromatography(hexane-ethyl acetate) to give the titled compound (56.6 mg) as acolorless amorphous product. (Yield 83%)

¹H-NMR (400 MHz, CDCl₃) δ 1.15 (s, 3H), 1.22 (s, 3H), 2.07 (s, 3H), 2.15(s, 3H), 2.25 (s, 3H), 3.74 (s, 3H), 4.01 (br s, 1H), 4.75 (d, J = 12.0Hz, 1H), 5.10 (d, J = 12.0 Hz, 1H), 5.46 (s, 1H), 6.22 (dd, J = 11.2,2.4 Hz, 1H), 6.43 (td, J = 8.3, 2.4 Hz, 1H), 6.58 (d, J = 8.1 Hz, 1H),6.90-6.96 (m, 3H), 6.99 (d, J = 2.9 Hz, 1H), 7.03 (dd, J = 8.8, 2.9 Hz,1H)

Example 36-(4-Aminoacetoxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinolinemonohydrochloride (Compound No. 3-1)

6-(4-t-Butoxycarbonylaminoacetoxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Reference Compound No. 4-1, 20.1 mg, 0.034 mmol) was dissolved in1,4-dioxane (0.5 mL), 4N hydrogen chloride/1,4-dioxane solution (34 μL)was added thereto, and then the mixture was stirred at room temperatureovernight. The reaction mixture was concentrated under reduced pressureto give the titled compound (17.5 mg) as a colorless solid. (Yield 98%)

¹H-NMR (400 MHz, DMSO-d₆) δ 1.09 (s, 3H), 1.18 (s, 3H), 2.01 (s, 3H),2.09 (s, 3H), 3.73 (s, 3H), 4.09-4.10 (m, 2H), 4.61 (d, J = 12.1 Hz,1H), 5.08 (d, J = 12.1 Hz, 1H), 5.47 (s, 1H), 6.35 (dd, J = 11.5, 2.4Hz, 1H), 6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.75- 6.87 (m, 1H), 6.80 (dd, J= 8.3, 2.2 Hz, 1H), 6.86 (d, J = 8.1 Hz, 1H), 6.91 (d, J = 2.2 Hz, 1H),7.02-7.06 (m, 1H), 7.25 (d, J = 8.3 Hz, 1H), 8.49 (br s, 3H)Using Compound No. 1-51, the following Compound No. 3-2 was obtained bya method similar to that of Compound No. 3-1.

5-(5-Fluoro-2-methylphenoxy- ¹H-NMR (400 MHz, DMSO-d₆)methyl)-6-[2-methoxy-4-(piper- δ 1.12 (s, 3H), 1.23 (s, 3H),idin-4-ylcarbonyloxy)phenyl]- 1.87-1.95 (m, 2H), 2.012,2,4-trimethyl-1,2-dihydro- (s, 3H), 2.10 (s, 3H), 2.10- quinolinemonohydrochloride 2.17 (m, 2H), 2.96-3.01 (m, 3H), (Compound No. 3-2)3.29-3.32 (m, 2H), 3.74

(s, 3H), 4.66 (d, J = 12.4 Hz, 1H), 5.11 (d, J = 12.4 Hz, 1H), 5.57 (s,1H), 6.34 (dd, J = 11.5, 2.4 Hz, 1H), 6.54 (td, J = 8.4, 2.4 Hz, 1H),6.79 (dd, J = 8.2, 2.2 Hz, 1H), 6.92 (d, J = 2.2 Hz, 1H), 6.93- 7.00 (m,2H), 6.96 (br s, 1H), 7.03-7.06 (m, 1H), 7.23 (d, J = 8.2 Hz, 1H), 8.88(br s, 1H), 9.08 (br s, 1H)

Example 45-(5-Fluoro-2-methylphenoxymethyl)-6-(2-methoxy-4-methylsulfonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 4-1)

5-(5-Fluoro-2-methylphenoxymethyl)-6-(4-hydroxy-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Reference Compound No. 3-1, 61.0 mg, 0.141 mmol) was dissolved inmethylene dichloride (2 mL), methanesulfonyl chloride (26 μL, 0.34 mmol)and triethylamine (92 μL, 0.66 mmol) were added thereto, and then themixture was stirred at room temperature overnight. The reaction mixturewas purified by silica gel column chromatography (hexane-ethyl acetate)to give the titled compound (58.0 mg) as a pale pink solid. (Yield 82%)

¹H-NMR (500 MHz, DMSO-d₆) δ 1.07 (s, 3H), 1.15 (s, 3H), 2.00 (s, 3H),2.07 (s, 3H), 3.37 (s, 3H), 3.75 (s, 3H), 4.60 (d, J = 12.2 Hz, 1H),5.06 (d, J = 12.2 Hz, 1H), 5.40 (s, 1H), 6.07 (s, 1H), 6.36 (dd, J =11.3, 2.5 Hz, 1H), 6.52 (td, J = 8.4, 2.5 Hz, 1H), 6.64 (d, J = 8.2 Hz,1H), 6.78 (d, J = 8.2 Hz, 1H), 6.93 (dd, J = 8.2, 2.3 Hz, 1H), 7.02-7.05(m, 1H), 7.03 (d, J = 2.3 Hz, 1H), 7.24 (d, J = 8.2 Hz, 1H)Using any compounds among Reference Compounds No. 3-1, 3-3 and 3-4, thefollowing Compounds (No. 4-2˜4-30) were obtained by a method similar tothat of Compound No. 4-1.

5-(5-Fluoro-2-methylphenoxy- ¹H-NMR (500 MHz, DMSO-d₆)methyl)-6-(2-methoxy-4-phen- δ 1.07 (s, 3H), 1.14 (s, 3H),ylsulfonyloxyphenyl)-2,2,4- 1.98 (s, 3H), 2.04 (s, 3H),trimethyl-1,2-dihydroquino- 3.55 (s, 3H), 4.47 (d, J = 11.9 line(Compound No. 4-2) Hz, 1H), 4.97 (d, J = 11.9 Hz,

1H), 5.39 (s, 1H), 6.06 (s, 1H), 6.35 (dd, J = 11.3, 2.5 Hz, 1H), 6.57(td, J = 8.4, 2.5 Hz, 1H), 6.59 (dd, J = 8.9, 2.4 Hz, 1H), 6.59 (d, J =2.4 Hz, 1H), 6.61 (d, J = 8.2 Hz, 1H), 6.71 (d, J = 8.2 Hz, 1H),7.05-7.08 (m, 1H), 7.12 (d, J = 8.9 Hz, 1H), 7.56-7.59 (m, 2H),7.76-7.81 (m, 3H) 6-[4-(2-Chlorophenylsulfonyl- ¹H-NMR (500 MHz,DMSO-d₆) oxy)-2-methoxyphenyl]-5-(5- δ 1.06 (s, 3H), 1.14 (s, 3H),fluoro-2-methylphenoxymeth- 1.96 (s, 3H), 2.02 (s, 3H),yl)-2,2,4-trimethyl-1,2-di- 3.60 (s, 3H), 4.45 (d, J = 12.1hydroquinoline (Compound No. Hz, 1H), 4.96 (d, J = 12.1 Hz, 4-3) 1H),5.39 (s, 1H), 6.06 (s,

1H), 6.30 (dd, J = 11.3, 2.4 Hz, 1H), 6.56 (td, J = 8.4, 2.4 Hz, 1H),6.60 (d, J = 8.2 Hz, 1H), 6.61-6.63 (m, 1H), 6.70 (d, J = 8.2 Hz, 1H),6.72 (d, J = 2.4 Hz, 1H), 7.03-7.06 (m, 1H), 7.13 (d, J = 8.2 Hz, 1H),7.47 (td, J = 7.9, 1.2 Hz, 1H), 7.77 (td, J = 7.9, 1.7 Hz, 1H), 7.84(dd, J = 7.9, 1.2 Hz, 1H), 7.88 (dd, J = 7.9, 1.7 Hz, 1H)6-[4-(3-Chlorophenylsulfonyl- ¹H-NMR (400 MHz, DMSO-d₆)oxy)-2-methoxyphenyl]-5-(5- δ 1.07 (s, 3H), 1.14 (s, 3H),fluoro-2-methylphenoxymeth- 1.98 (s, 3H), 2.04 (s, 3H),yl)-2,2,4-trimethyl-1,2-di- 3.60 (s, 3H), 4.50 (d, J = 12.0hydroquinoline (Compound No. Hz, 1H), 4.99 (d, J = 12.0 Hz, 4-4) 1H),5.39 (s, 1H), 6.07 (s,

1H), 6.32 (dd, J = 11.2, 2.5 Hz, 1H), 6.55 (td, J = 8.5, 2.5 Hz, 1H),6.61 (d, J = 8.1 Hz, 1H), 6.65 (dd, J = 8.2, 2.3 Hz, 1H), 6.71 (d, J =2.3 Hz, 1H), 6.72 (d, J = 8.1 Hz, 1H), 7.03-7.06 (m, 1H), 7.16 (d, J =8.2 Hz, 1H), 7.61 (t, J = 8.0 Hz, 1H), 7.77 (ddd, J = 8.0, 1.8, 1.0 Hz,1H), 7.88 (ddd, J = 8.0, 1.8, 1.0 Hz, 1H), 7.91 (t, J = 1.8 Hz, 1H)6-[4-(4-Chlorophenylsulfonyl- ¹H-NMR (500 MHz, DMSO-d₆)oxy)-2-methoxyphenyl]-5-(5- δ 1.07 (s, 3H), 1.14 (s, 3H),fluoro-2-methylphenoxymeth- 1.99 (s, 3H), 2.04 (s, 3H),yl)-2,2,4-trimethyl-1,2-di- 3.59 (s, 3H), 4.49 (d, J = 12.1hydroquinoline (Compound No. Hz, 1H), 4.99 (d, J = 12.1 Hz, 4-5) 1H),5.40 (s, 1H), 6.07 (s,

1H), 6.37 (dd, J = 11.3, 2.5 Hz, 1H), 6.56 (td, J = 8.5, 2.5 Hz, 1H),6.59 (dd, J = 8.4, 2.1 Hz, 1H), 6.61 (d, J = 8.2 Hz, 1H), 6.67 (d, J =2.1 Hz, 1H), 6.72 (d, J = 8.2 Hz, 1H), 7.04-7.07 (m, 1H), 7.14 (d, J =8.4 Hz, 1H), 7.63 (d, J = 8.9 Hz, 2H), 7.81 (d, J = 8.9 Hz, 2H)5-(5-Fluoro-2-methylphenoxy- ¹H-NMR (500 MHz, DMSO-d₆)methyl)-6-[2-methoxy-4-(3- δ 1.06 (s, 3H), 1.14 (s, 3H),methoxyphenylsulfonyloxy) 1.98 (s, 3H), 2.04 (s, 3H),phenyl]-2,2,4-trimethyl-1,2-di- 3.58 (s, 3H), 3.79 (s, 3H), 4.50hydroquinoline (Compound (d, J = 12.1 Hz, 1H), 4.99 No. 4-6) (d, J =12.1 Hz, 1H), 5.39 (s,

1H), 6.06 (s, 1H), 6.31 (dd, J = 11.6, 2.4 Hz, 1H), 6.55 (td, J = 8.4,2.4 Hz, 1H), 6.61 (d, J = 8.2 Hz, 1H), 6.63 (dd, J = 8.3, 2.4 Hz, 1H),6.66 (d, J = 2.4 Hz, 1H), 6.72 (d, J = 8.2 Hz, 1H), 7.03-7.06 (m, 1H),7.14 (d, J = 8.3 Hz, 1H), 7.32-7.35 (m, 3H), 7.47 (t, J = 8.2 Hz, 1H)5-(5-Fluoro-2-methylphenoxy- ¹H-NMR (500 MHz, DMSO-d₆)methyl)-6-[2-methoxy-4-(4- δ 1.07 (s, 3H), 1.14 (s, 3H),methoxyphenylsulfonyloxy) 1.99 (s, 3H), 2.05 (s, 3H),phenyl]-2,2,4-trimethyl-1,2-di- 3.58 (s, 3H), 3.82 (s, 3H), 4.49hydroquinoline (Compound (d, J = 12.1 Hz, 1H), 4.99 No. 4-7) (d, J =12.1 Hz, 1H), 5.39 (s,

1H), 6.06 (s, 1H), 6.35 (dd, J = 11.6, 2.5 Hz, 1H), 6.55 (td, J = 8.4,2.5 Hz, 1H), 6.57 (dd, J = 8.2, 2.3 Hz, 1H), 6.60 (d, J = 2.3 Hz, 1H),6.61 (d, J = 8.1 Hz, 1H), 6.72 (d, J = 8.1 Hz, 1H), 7.04-7.07 (m, 1H),7.05 (d, J = 9.2 Hz, 2H), 7.12 (d, J = 8.2 Hz, 1H), 7.70 (d, J = 9.2 Hz,2H) 5-(5-Fluoro-2-methylphenoxy- ¹H-NMR (500 MHz, DMSO-d₆)methyl)-6-(2-methoxy-4-tri- δ 1.09 (s, 3H), 1.16 (s, 3H),fluoromethylsulfonyloxyphenyl)- 1.99 (s, 3H), 2.06 (s, 3H),2,2,4-trimethyl-1,2-dihydro- 3.77 (s, 3H), 4.55 (d, J = 11.9 quinoline(Compound No. 4-8) Hz, 1H), 5.03 (d, J = 11.9 Hz,

1H), 5.41 (s, 1H), 6.11 (s, 1H), 6.36 (dd, J = 11.6, 2.4 Hz, 1H), 6.53(td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.78 (d, J = 8.2Hz, 1H), 7.02-7.05 (m, 1H), 7.03 (dd, J = 8.4, 2.4 Hz, 1H), 7.18 (d, J =2.4 Hz, 1H), 7.31 (d, J = 8.4. Hz, 1H) 6-(4-Benzylsulfonyloxy-2- ¹H-NMR(500 MHz, DMSO-d₆) methoxyphenyl)-5-(5-fluoro-2- δ 1.06 (s, 3H), 1.15(s, 3H), methylphenoxymethyl)-2,2,4- 2.01 (s, 3H), 2.06 (s, 3H),trimethyl-1,2-dihydroquino- 3.70 (s, 3H), 4.58 (d, J = 12.1 line(Compound No. 4-9) Hz, 1H), 4.97 (s, 2H), 5.05

(d, J = 12.1 Hz, 1H), 5.40 (s, 1H), 6.07 (s, 1H), 6.37 (dd, J = 11.3,2.4 Hz, 1H), 6.52 (td, J = 8.4, 2.4 Hz, 1H), 6.63 (d, J = 8.2 Hz, 1H),6.76 (d, J = 8.2 Hz, 1H), 6.81 (d, J = 2.3 Hz, 1H), 6.83 (dd, J = 8.2,2.3 Hz, 1H), 7.02-7.05 (m, 1H), 7.21 (d, J = 8.2 Hz, 1H), 7.41-7.44 (m,3H), 7.47-7.49 (m, 2H) 5-(5-Fluoro-2-methylphenoxy- ¹H-NMR (400 MHz,DMSO-d₆) methyl)-6-[4-(furan-2-yl- δ 1.08 (s, 3H), 1.15 (s, 3H),sulfonyloxy)-2-methoxyphenyl]- 1.98 (s, 3H), 2.04 (s, 3H),2,2,4-trimethyl-1,2-dihydro- 3.63 (s, 3H), 4.49 (d, J = 11.8 quinoline(Compound No. 4-10) Hz, 1H), 4.99 (d, J = 11.8 Hz,

1H), 5.40 (s, 1H), 6.08 (s, 1H), 6.36 (dd, J = 11.5, 2.4 Hz, 1H), 6.56(td, J = 8.4, 2.4 Hz, 1H), 6.60 (dd, J = 8.1, 2.6 Hz, 1H), 6.62 (d, J =8.3 Hz, 1H), 6.65 (d, J = 2.6 Hz, 1H), 6.70 (dd, J = 3.7, 1.8 Hz, 1H),6.73 (d, J = 8.3 Hz, 1H), 7.04-7.08 (m, 1H), 7.17 (d, J = 8.1 Hz, 1H),7.24 (dd, J = 3.7, 0.9 Hz, 1H), 8.19 (dd, J = 1.8, 0.9 Hz, 1H)5-(5-Fluoro-2-methylphenoxy- ¹H-NMR (400 MHz, DMSO-d₆)methyl)-6-(2-methoxy-4-prop- δ 1.01 (t, J = 7.5 Hz, 3H),ylsulfonyloxyphenyl)-2,2,4- 1.07 (s, 3H), 1.15 (s, 3H), 1.83trimethyl-1,2-dihydroquino- (sextet, J = 7.5 Hz, 2H), line (Compound No.4-11) 2.00 (s, 3H), 2.06 (s, 3H), 3.48

(t, J = 7.5 Hz, 2H), 3.75 (s, 3H), 4.58 (d, J = 12.0 Hz, 1H), 5.05 (d, J= 12.0 Hz, 1H), 5.40 (s, 1H), 6.07 (s, 1H), 6.36 (dd, J = 11.5, 2.4 Hz,1H), 6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.1 Hz, 1H), 6.77 (d,J = 8.1 Hz, 1H), 6.91 (dd, J = 8.3, 2.4 Hz, 1H), 6.98 (d, J = 2.4 Hz,1H), 7.01-7.05 (m, 1H), 7.23 (d, J = 8.3 Hz, 1H)6-(4-Ethylsulfonyloxy-2-meth- ¹H-NMR (400 MHz, DMSO-d₆)oxyphenyl)-5-(5-fluoro-2- δ 1.07 (s, 3H), 1.15 (s, 3H),methylphenoxymethyl)-2,2,4- 1.35 (t, J = 7.3 Hz, 3H), 2.00trimethyl-1,2-dihydroquinoline (s, 3H), 2.06 (s, 3H), 3.50 (Compound No.4-12) (q, J = 7.3 Hz, 2H), 3.75 (s,

3H), 4.58 (d, J = 12.0 Hz, 1H), 5.05 (d, J = 12.0 Hz, 1H), 5.40 (s, 1H),6.07 (s, 1H), 6.36 (dd, J = 11.5, 2.5 Hz, 1H), 6.53 (td, J = 8.4, 2.5Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.77 (d, J = 8.2 Hz, 1H), 6.91 (dd, J= 8.3, 2.4 Hz, 1H), 6.98 (d, J = 2.4 Hz, 1H), 7.01-7.05 (m, 1H), 7.23(d, J = 8.3 Hz, 1H) 5-(5-Fluoro-2-methylphenoxy- ¹H-NMR (500 MHz,DMSO-d₆) methyl)-6-(4-isopropylsulfon- δ 1.07 (s, 3H), 1.15 (s, 3H),yloxy-2-methoxyphenyl)-2,2,4- 1.42 (d, J = 6.7 Hz, 6H), 2.01trimethyl-1,2-dihydro- (s, 3H), 2.06 (s, 3H), 3.70 quinoline (CompoundNo. 4-13) (septet, J = 6.7 Hz, 1H), 3.75

(s, 3H), 4.58 (d, J = 12.2 Hz, 1H), 5.05 (d, J = 12.2 Hz, 1H), 5.40 (s,1H), 6.07 (s, 1H), 6.37 (dd, J = 11.3, 2.5 Hz, 1H), 6.53 (td, J = 8.5,2.5 Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.77 (d, J = 8.2 Hz, 1H), 6.90(dd, J = 8.2, 2.4 Hz, 1H), 6.95 (d, J = 2.4 Hz, 1H), 7.02-7.05 (m, 1H),7.23 (d, J = 8.2 Hz, 1H) 6-(4-Butylsulfonyloxy-2-meth- ¹H-NMR (400 MHz,DMSO-d₆) oxyphenyl)-5-(5-fluoro-2- δ 0.89 (t, J = 7.6 Hz, 3H),methylphenoxymethyl)-2,2,4- 1.07 (s, 3H), 1.15 (s, 3H), 1.42trimethyl-1,2-dihydroquinoline (sextet, J = 7.6 Hz, 2H), (Compound No.4-14) 1.78 (quintet, J = 7.6 Hz, 2H),

2.00 (s, 3H), 2.06 (s, 3H), 3.49 (t, J = 7.6 Hz, 2H), 3.75 (s, 3H), 4.58(d, J = 12.1 Hz, 1H), 5.05 (d, J = 12.1 Hz, 1H), 5.40 (s, 1H), 6.07 (s,1H), 6.36 (dd, J = 11.5, 2.4 Hz, 1H), 6.53 (td, J = 8.4, 2.4 Hz, 1H),6.64 (d, J = 8.2 Hz, 1H), 6.77 (d, J = 8.2 Hz, 1H), 6.92 (dd, J = 8.3,2.3 Hz, 1H), 6.98 (d, J = 2.3 Hz, 1H), 7.01-7.05 (m, 1H), 7.23 (d, J =8.3 Hz, 1H) 5-(5-Fluoro-2-methylphenoxy- ¹H-NMR (400 MHz, DMSO-d₆)methyl)-6-[2-methoxy-4-(2- δ 1.06 (s, 3H), 1.14 (s, 3H),methylphenylsulfonyloxy)phen- 1.97 (s, 3H), 2.03 (s, 3H),yl]-2,2,4-trimethyl-1,2-di- 2.64 (s, 3H), 3.55 (s, 3H), 4.45hydroquinoline (Compound No. (d, J = 11.7 Hz, 1H), 4.96 4-15) (d, J =11.7 Hz, 1H), 5.39 (s,

1H), 6.06 (s, 1H), 6.32 (dd, J = 11.4, 2.5 Hz, 1H), 6.56 (td, J = 8.2,2.5 Hz, 1H), 6.56- 6.58 (m, 1H), 6.58 (d, J = 2.2 Hz, 1H), 6.60 (d, J =8.3 Hz, 1H), 6.70 (d, J = 8.3 Hz, 1H), 7.04-7.07 (m, 1H), 7.11 (d, J =8.1 Hz, 1H), 7.30-7.34 (m, 1H), 7.53 (d, J = 7.7 Hz, 1H), 7.66 (td, J =7.7, 1.2 Hz, 1H), 7.71 (dd, J = 7.7, 1.2 Hz, 1H)5-(5-Fluoro-2-methylphenoxy- ¹H-NMR (500 MHz, DMSO-d₆)methyl)-6-[4-(2-fluorophenyl- δ 1.07 (s, 3H), 1.14 (s, 3H),sulfonyloxy)-2-methoxyphen- 1.97 (s, 3H), 2.03 (s, 3H),yl]-2,2,4-trimethyl-1,2-di- 3.60 (s, 3H), 4.46 (d, J = 12.1hydroquinoline (Compound No. Hz, 1H), 4.96 (d, J = 12.1 Hz, 4-16) 1H),5.39 (s, 1H), 6.06 (s,

1H), 6.31 (dd, J = 11.3, 2.5 Hz, 1H), 6.56 (td, J = 8.4, 2.5 Hz, 1H),6.59 (d, J = 8.2 Hz, 1H), 6.63 (dd, J = 8.3, 2.4 Hz, 1H), 6.70 (d, J =2.4 Hz, 1H), 6.71 (d, J = 8.2 Hz, 1H), 7.04-7.07 (m, 1H), 7.14 (d, J =8.3 Hz, 1H), 7.34 (td, J = 7.7, 0.9 Hz, 1H), 7.55-7.58 (m, 1H), 7.73(td, J = 7.5, 1.9 Hz, 1H), 7.83-7.88 (m, 1H)6-(2-Methoxy-4-methylsulfon- ¹H-NMR (500 MHz, CDCl₃)yloxyphenyl)-5-(2-methoxy-5- δ 1.05 (s, 3H), 1.27 (s, 3H),nitrophenoxymethyl)-2,2,4- 2.27 (s, 3H), 3.15 (s, 3H),trimethyl-1,2-dihydroquino- 3.78 (s, 3H), 3.84 (s, 3H), 4.78 line(Compound No. 4-17) (d, J = 12.2 Hz, 1H), 5.35

(d, J = 12.2 Hz, 1H), 5.47 (s, 1H), 6.56 (d, J = 8.2 Hz, 1H), 6.78 (d, J= 9.1 Hz, 1H), 6.84 (d, J = 8.2 Hz, 1H), 6.85 (d, J = 2.4 Hz, 1H), 6.86(dd, J = 8.0, 2.4 Hz, 1H), 7.27 (d, J = 2.7 Hz, 1H), 7.31 (d, J = 8.0Hz, 1H), 7.78 (dd, J = 9.1, 2.7 Hz, 1H) 5-(2-Methoxy-5-nitrophenoxy-¹H-NMR (500 MHz, DMSO-d₆) methyl)-6-(2-methoxy-4-prop- δ 0.99 (t, J =7.3 Hz, 3H), ylsulfonyloxyphenyl)-2,2,4- 1.06 (s, 3H), 1.18 (s, 3H),1.81 trimethyl-1,2-dihydroquino- (tq, J = 7.6, 7.3 Hz, 2H), line(Compound No. 4-18) 2.14 (s, 3H), 3.44 (t, J = 7.6

Hz, 2H), 3.71 (s, 3H), 3.82 (s, 3H), 4.63 (d, J = 11.9 Hz, 1H), 5.23 (d,J = 11.9 Hz, 1H), 5.41 (s, 1H), 6.05 (s, 1H), 6.62 (d, J = 8.2 Hz, 1H),6.75 (d, J = 8.2 Hz, 1H), 6.83 (dd, J = 8.2, 2.4 Hz, 1H), 6.92 (d, J =2.4 Hz, 1H), 7.08 (d, J = 9.1 Hz, 1H), 7.19 (d, J = 8.2 Hz, 1H), 7.32(d, J = 2.7 Hz, 1H), 7.81 (dd, J = 9.1, 2.7 Hz, 1H)6-(4-Cyclopropylsulfonyloxy- ¹H-NMR (400 MHz, CDCl₃)2-methoxyphenyl)-5-(2-meth- δ 1.04 (s, 3H), 1.08-1.12 (m,oxy-5-nitrophenoxymethyl)- 2H), 1.23-1.26 (m, 2H), 1.272,2,4-trimethyl-1,2-dihydro- (s, 3H), 2.27 (s, 3H), 2.55-2.61 quinoline(Compound No. 4-19) (m, 1H), 3.77 (s, 3H), 3.84

(s, 3H), 4.77 (d, J = 12.4 Hz, 1H), 5.35 (d, J = 12.4 Hz, 1H), 5.47 (s,1H), 6.07 (s, 1H), 6.56 (d, J = 8.2 Hz, 1H), 6.78 (d, J = 9.0 Hz, 1H),6.85 (d, J = 8.2 Hz, 1H), 6.86 (d, J = 2.2 Hz, 1H), 6.90 (dd, J = 8.3,2.2 Hz, 1H), 7.27 (d, J = 2.7 Hz, 1H), 7.30 (d, J = 8.3 Hz, 1H), 7.78(dd, J = 9.0, 2.7 Hz, 1H) 6-(4-Isopropylsulfonyloxy-2- ¹H-NMR (500 MHz,DMSO-d₆) methoxyphenyl)-5-(2-methoxy- δ 1.06 (s, 3H), 1.18 (s, 3H),5-nitrophenoxymethyl)-2,2,4- 1.39 (d, J = 6.7 Hz, 6H), 2.14trimethyl-1,2-dihydro- (s, 3H), 3.62-3.67 (m, 1H), quinoline (CompoundNo. 4-20) 3.71 (s, 3H), 3.82 (s, 3H), 4.61

(d, J = 11.9 Hz, 1H), 5.23 (d, J = 11.9 Hz, 1H), 5.41 (s, 1H), 6.05 (s,1H), 6.62 (d, J = 8.1 Hz, 1H), 6.74 (d, J = 8.1 Hz, 1H), 6.82 (dd, J =8.2, 2.4 Hz, 1H), 6.89 (d, J = 2.4 Hz, 1H), 7.08 (d, J = 9.1 Hz, 1H),7.18 (d, J = 8.2 Hz, 1H), 7.32 (d, J = 2.7 Hz, 1H), 7.81 (dd, J = 9.1,2.7 Hz, 1H) 6-(4-Isobutylsulfonyloxy-2- ¹H-NMR (400 MHz, DMSO-d₆)methoxyphenyl)-5-(2-methoxy- δ 1.03 (d, J = 6.6 Hz, 6H),5-nitrophenoxymethyl)-2,2,4- 1.06 (s, 3H), 1.18 (s, 3H), 2.14trimethyl-1,2-dihydroquino- (s, 3H), 2.18-2.25 (m, 1H), line (CompoundNo. 4-21) 3.39 (d, J = 6.6 Hz, 2H), 3.71

(s, 3H), 3.82 (s, 3H), 4.62 (d, J = 12.1 Hz, 1H), 5.23 (d, J = 12.1 Hz,1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.62 (d, J = 8.1 Hz, 1H), 6.75 (d, J =8.1 Hz, 1H), 6.83 (dd, J = 8.3, 2.2 Hz, 1H), 6.93 (d, J = 2.2 Hz, 1H),7.08 (d, J = 9.0 Hz, 1H), 7.19 (d, J = 8.3 Hz, 1H), 7.32 (d, J = 2.7 Hz,1H), 7.81 (dd, J = 9.0, 2.7 Hz, 1H) 5-(2-Methoxy-5-nitrophenoxy- ¹H-NMR(500 MHz, DMSO-d₆) methyl)-6-[2-methoxy-4-(3,3,3- δ 1.06 (s, 3H), 1.18(s, 3H), trifluoropropylsulfonyl- 2.14 (s, 3H), 2.92-2.95 (m, 2H),oxy)phenyl]-2,2,4-trimethyl- 3.71 (s, 3H), 3.78-3.821,2-dihydroquinoline (Compound (m, 2H), 3.82 (s, 3H), 4.62 No. 4-22) (d,J = 11.9 Hz, 1H), 5.23 (d,

J = 11.9 Hz, 1H), 5.41 (s, 1H), 6.06 (s, 1H), 6.62 (d, J = 8.2 Hz, 1H),6.75 (d, J = 8.2 Hz, 1H), 6.89 (dd, J = 8.3, 2.4 Hz, 1H), 7.01 (d, J =2.4 Hz, 1H), 7.07 (d, J = 9.1 Hz, 1H), 7.21 (d, J = 8.3 Hz, 1H), 7.32(d, J = 2.6 Hz, 1H), 7.81 (dd, J = 9.1, 2.6 Hz, 1H)6-(4-Ethylsulfonyloxy-2-meth- ¹H-NMR (400 MHz, DMSO-d₆)oxyphenyl)-5-(2-methyl-5- δ 0.93 (s, 3H), 1.18 (s, 3H),nitrophenoxymethyl)-2,2,4- 1.35 (t, J = 7.3 Hz, 3H), 2.13trimethyl-1,2-dihydroquinoline (s, 3H), 2.17 (s, 3H), 3.51 (Compound No.4-23) (q, J = 7.3 Hz, 2H), 3.76 (s,

3H), 4.76 (d, J = 12.6 Hz, 1H), 5.29 (d, J = 12.6 Hz, 1H), 5.41 (s, 1H),6.07 (s, 1H), 6.62 (d, J = 8.3 Hz, 1H), 6.78 (d, J = 8.3 Hz, 1H), 6.95(dd, J = 8.2, 2.3 Hz, 1H), 6.99 (d, J = 2.3 Hz, 1H), 7.15 (d, J = 2.1Hz, 1H), 7.31 (d, J = 8.2 Hz, 1H), 7.33 (d, J = 8.2 Hz, 1H), 7.64 (dd, J= 8.2, 2.1 Hz, 1H) 6-(4-Butylsulfonyloxy-2-meth- ¹H-NMR (500 MHz,DMSO-d₆) oxyphenyl)-5-(2-methyl-5- δ 0.89 (t, J = 7.3 Hz, 3H),nitrophenoxymethyl)-2,2,4- 0.93 (s, 3H), 1.18 (s, 3H), 1.38-trimethyl-1,2-dihydroquinoline 1.45 (m, 2H), 1.75-1.81 (Compound No.4-24) (m, 2H), 2.13 (s, 3H), 2.17

(s, 3H), 3.48-3.52 (m, 2H), 3.76 (s, 3H), 4.76 (d, J = 12.5 Hz, 1H),5.29 (d, J = 12.5 Hz, 1H), 5.41 (s, 1H), 6.07 (s, 1H), 6.62 (d, J = 8.2Hz, 1H), 6.79 (d, J = 8.2 Hz, 1H), 6.95 (dd, J = 8.2, 2.3 Hz, 1H), 6.99(d, J = 2.3 Hz, 1H), 7.15 (d, J = 2.2 Hz, 1H), 7.31 (d, J = 8.2 Hz, 1H),7.33 (d, J = 8.2 Hz, 1H), 7.63 (dd, J = 8.2, 2.2 Hz, 1H)6-(2-Methoxy-4-propylsulfon- ¹H-NMR (500 MHz, DMSO-d₆)yloxyphenyl)-5-(2-methyl-5- δ 0.93 (s, 3H), 1.01 (t, J =nitrophenoxymethyl)-2,2,4- 7.5 Hz, 3H), 1.18 (s, 3H), 1.80-trimethyl-1,2-dihydroquinoline 1.87 (m, 2H), 2.13 (s, 3H), (Compound No.4-25) 2.17 (s, 3H), 3.49 (t, J = 7.6

Hz, 2H), 3.76 (s, 3H), 4.76 (d, J = 12.5 Hz, 1H), 5.29 (d, J = 12.5 Hz,1H), 5.41 (s, 1H), 6.07 (s, 1H), 6.62 (d, J = 8.2 Hz, 1H), 6.79 (d, J =8.2 Hz, 1H), 6.94 (dd, J = 8.2, 2.4 Hz, 1H), 6.98 (d, J = 2.4 Hz, 1H),7.15 (d, J = 2.2 Hz, 1H), 7.31 (d, J = 8.2 Hz, 1H), 7.33 (d, J = 8.0 Hz,1H), 7.64 (dd, J = 8.0, 2.2 Hz, 1H) 6-(4-Isopropylsulfonyloxy-2- ¹H-NMR(500 MHz, DMSO-d₆) methoxyphenyl)-5-(2-methyl- δ 0.93 (s, 3H), 1.18 (s,3H), 5-nitrophenoxymethyl)-2,2,4- 1.42 (d, J = 6.7 Hz, 6H), 2.13trimethyl-1,2-dihydroquino- (s, 3H), 2.17 (s, 3H), 3.68- line (CompoundNo. 4-26) 3.74 (m, 1H), 3.76 (s, 3H), 4.75

(d, J = 12.5 Hz, 1H), 5.28 (d, J = 12.5 Hz, 1H), 5.41 (s, 1H), 6.07 (s,1H), 6.62 (d, J = 8.2 Hz, 1H), 6.79 (d, J = 8.2 Hz, 1H), 6.93 (dd, J =8.2, 2.2 Hz, 1H), 6.95 (d, J = 2.2 Hz, 1H), 7.16 (d, J = 2.1 Hz, 1H),7.31 (d, J = 8.2 Hz, 1H), 7.33 (d, J = 8.2 Hz, 1H), 7.64 (dd, J = 8.2,2.1 Hz, 1H) 6-(4-Cyclopropylsulfonyloxy- ¹H-NMR (500 MHz, DMSO-d₆)2-methoxyphenyl)-5-(5-fluoro- δ 0.89-0.94 (m, 2H), 1.04-1.082-methylphenoxymethyl)- (m, 2H), 1.08 (s, 3H), 1.152,2,4-trimethyl-1,2-dihydro- (s, 3H), 2.01 (s, 3H), 2.07 quinoline(Compound No. 4-27) (s, 3H), 3.01 (tt, J = 7.9, 4.9

Hz, 1H), 3.75 (s, 3H), 4.56 (d, J = 12.1 Hz, 1H), 5.04 (d, J = 12.1 Hz,1H), 5.41 (s, 1H), 6.07 (s, 1H), 6.38 (dd, J = 11.3, 2.4 Hz, 1H), 6.53(td, J = 8.6, 2.4 Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.78 (d, J = 8.2Hz, 1H), 6.93 (dd, J = 8.2, 2.4 Hz, 1H), 7.01-7.05 (m, 1H), 7.03 (d, J =2.4 Hz, 1H), 7.22 (d, J = 8.2 Hz, 1H) 5-(5-Fluoro-2-methylphenoxy-¹H-NMR (500 MHz, DMSO-d₆) methyl)-6-(4-isobutylsulfon- δ 1.06 (d, J =7.0 Hz, 6H), yloxy-2-methoxyphenyl)-2,2,4- 1.07 (s, 3H), 1.15 (s, 3H),2.00 trimethyl-1,2-dihydroquino- (s, 3H), 2.06 (s, 3H), 2.21- line(Compound No. 4-28) 2.26 (m, 1H), 3.43 (d, J = 6.4

Hz, 2H), 3.75 (s, 3H), 4.59 (d, J = 12.1 Hz, 1H), 5.05 (d, J = 12.1 Hz,1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.36 (dd, J = 11.5, 2.6 Hz, 1H), 6.53(td, J = 8.5, 2.6 Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.77 (d, J = 8.2Hz, 1H), 6.92 (dd, J = 8.3, 2.2 Hz, 1H), 6.98 (d, J = 2.2 Hz, 1H),7.01-7.05 (m, 1H), 7.23 (d, J = 8.3 Hz, 1H) 6-(4-Cyclopentylsulfonyloxy-¹H-NMR (500 MHz, DMSO-d₆) 2-methoxyphenyl)-5-(5-fluoro- δ 1.07 (s, 3H),1.15 (s, 3H), 2-methylphenoxymethyl)- 1.57-1.65 (m, 2H), 1.68-1.752,2,4-trimethyl-1,2-dihydro- (m, 2H), 1.95-2.02 (m, 2H), 2.01 quinoline(Compound No. 4-29) (s, 3H), 2.04-2.11 (m, 2H),

2.06 (s, 3H), 3.75 (s, 3H), 3.94 (tt, J = 8.9, 6.7 Hz, 1H), 4.57 (d, J =11.9 Hz, 1H), 5.05 (d, J = 11.9 Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H),6.37 (dd, J = 11.3, 2.4 Hz, 1H), 6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.64(d, J = 8.2 Hz, 1H), 6.77 (d, J = 8.2 Hz, 1H), 6.90 (dd, J = 8.2, 2.1Hz, 1H), 6.95 (d, J = 2.1 Hz, 1H), 7.02- 7.05 (m, 1H), 7.23 (d, J = 8.2Hz, 1H) 5-(5-Fluoro-2-methylphenoxy- ¹H-NMR (500 MHz, DMSO-d₆)methyl)-6-[2-methoxy-4-(3,3,3- δ 1.07 (s, 3H), 1.15 (s, 3H),trifluoroproprylsulfonyl- 2.00 (s, 3H), 2.06 (s, 3H),oxy)phenyl]-2,2,4-trimethyl- 2.90-3.00 (m, 2H), 3.75 (s, 3H),1,2-dihydroquinoline 3.83-3.87 (m, 2H), 4.59 (Compound No. 4-30) (d, J =12.1 Hz, 1H), 5.05 (d,

J = 12.1 Hz, 1H), 5.40 (s, 1H), 6.07 (s, 1H), 6.35 (dd, J = 11.5, 2.4Hz, 1H), 6.52 (td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.78(d, J = 8.2 Hz, 1H), 6.97 (dd, J = 8.2, 2.3 Hz, 1H), 7.01-7.05 (m, 1H),7.06 (d, J = 2.3 Hz, 1H), 7.25 (d, J = 8.2 Hz, 1H)

Example 55-(5-Fluoro-2-methylphenoxymethyl)-6-(2-methoxy-4-methoxycarbonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 5-1)

5-(5-Fluoro-2-methylphenoxymethyl)-6-(4-hydroxy-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Reference Compound No. 3-1, 25.0 mg, 0.058 mmol) was dissolved intetrahydrofuran (0.5 mL), triethylamine (23 μL, 0.17 mmol) and methylchlorocarbonate (6.8 μL, 0.088 mmol) were added thereto, and then themixture was stirred at room temperature for 20 minutes. The reactionmixture was purified by silica gel column chromatography (hexane-ethylacetate) to give the titled compound (28.0 mg) as a colorless amorphousproduct. (Yield 99%)

¹H-NMR (500 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.15 (s, 3H), 2.01 (s, 3H),2.07 (s, 3H), 3.72 (s, 3H), 3.83 (s, 3H), 4.61 (d, J = 12.2 Hz, 1H),5.07 (d, J = 12.2 Hz, 1H), 5.39 (s, 1H), 6.04 (s, 1H), 6.35 (dd, J =11.3, 2.4 Hz, 1H), 6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.63 (d, J = 8.2 Hz,1H), 6.78 (d, J = 8.2 Hz, 1H), 6.82 (dd, J = 8.2, 2.3 Hz, 1H), 6.98 (d,J = 2.3 Hz, 1H), 7.02-7.05 (m, 1H), 7.19 (d, J = 8.2 Hz, 1H)Using any compounds among Reference Compounds No. 3-1, 3-3 and 3-4, thefollowing Compounds (No. 5-2˜5-10) were obtained by a method similar tothat of Compound No. 5-1.

5-(5-Fluoro-2-methylphenoxymethyl)-6-(2-methoxy-4-phenoxycarbonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 5-2)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.02 (s, 3H),2.07 (s, 3H), 3.75 (s, 3H), 4.62 (d, J = 12.2 Hz, 1H), 5.08 (d, J = 12.2Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.36 (dd, J = 11.3, 2.4 Hz, 1H),6.52 (td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.79 (d, J =8.2 Hz, 1H), 6.97 (dd, J = 8.2, 2.4 Hz, 1H), 7.02-7.05 (m, 1H), 7.14 (d,J = 2.4 Hz, 1H), 7.23 (d, J = 8.2 Hz, 1H), 7.34 (t, J = 7.6 Hz, 1H),7.39 (d, J = 7.6 Hz, 2H), 7.49 (t, J = 7.6 Hz, 2H)6-[4-(2-Chlorophenoxycarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 5-3)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.01 (s, 3H),2.07 (s, 3H), 3.76 (s, 3H), 4.61 (d, J = 11.9 Hz, 1H), 5.07 (d, J = 11.9Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.37 (dd, J = 11.5, 2.4 Hz, 1H),6.52 (td, J = 8.4, 2.5 Hz, 1H), 6.64 (d, J = 8.2 Hz, 1H), 6.79 (d, J =8.2 Hz, 1H), 6.96 (dd, J = 8.3, 2.3 Hz, 1H), 7.01-7.05 (m, 1H), 7.10 (d,J = 2.3 Hz, 1H), 7.25 (d, J = 8.3 Hz, 1H), 7.39 (td, J = 7.9, 1.6 Hz,1H), 7.48 (td, J = 7.9, 1.7 Hz, 1H), 7.61 (dd, J = 7.9, 1.6 Hz, 1H),7.66 (dd, J = 7.9, 1.7 Hz, 1H)6-[4-(4-Chlorophenoxycarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 5-4)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.01 (s, 3H),2.07 (s, 3H), 3.75 (s, 3H), 4.61 (d, J = 12.1 Hz, 1H), 5.07 (d, J = 12.1Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.36 (dd, J = 11.3, 2.4 Hz, 1H),6.52 (td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.1 Hz), 1H), 6.79 (d, J =8.1 Hz, 1H), 6.97 (dd, J = 8.2, 2.4 Hz, 1H), 7.02-7.05 (m, 1H), 7.15 (d,J = 2.4 Hz, 1H), 7.23 (d, J = 8.2 Hz, 1H), 7.45 (d, J = 9.1 Hz, 2H),7.55 (d, J = 9.1 Hz, 2H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-methoxyphenoxycarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 5-5)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.01 (s, 3H),2.07 (s, 3H), 3.76 (s, 3H), 3.86 (s, 3H), 4.62 (d, J = 12.1 Hz, 1H),5.07 (d, J = 12.1 Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.36 (dd, J =11.3, 2.4 Hz, 1H), 6.52 (td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.2 Hz,1H), 6.78 (d, J = 8.2 Hz, 1H), 6.91 (dd, J = 8.2, 2.3 Hz, 1H), 7.01 (td,J = 8.0, 1.4 Hz, 1H), 7.02-7.05 (m, 1H), 7.05 (d, J = 2.3 Hz, 1H), 7.20(dd, J = 8.0, 1.4 Hz, 1H), 7.23 (d, J = 8.2 Hz, 1H), 7.31 (td, J = 8.0,1.6 Hz, 1H), 7.35 (dd, J = 8.0, 1.6 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-methoxyphenoxycarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 5-6)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.01 (s, 3H),2.07 (s, 3H), 3.75 (s, 3H), 3.77 (s, 3H), 4.61 (d, J = 12.1 Hz, 1H),5.07 (d, J = 12.1 Hz, 1H), 5.40 (s, 1H), 6.05 (s, 1H), 6.36 (dd, J =11.6, 2.4 Hz, 1H), 6.52 (td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.2 Hz,1H), 6.79 (d, J = 8.2 Hz, 1H), 6.95 (dd, J = 8.2, 2.4 Hz, 1H), 7.00 (d,J = 9.2 Hz, 2H), 7.02-7.05 (m, 1H), 7.12 (d, J = 2.4 Hz, 1H), 7.23 (d, J= 8.2 Hz, 1H), 7.30 (d, J = 9.2 Hz, 2H)6-(4-Benzyloxycarbonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 5-7)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.15 (s, 3H), 2.01 (s, 3H),2.06 (s, 3H), 3.72 (s, 3H), 4.61 (d, J = 12.1 Hz, 1H), 5.07 (d, J = 12.1Hz, 1H), 5.27 (s, 2H), 5.39 (s, 1H), 6.04 (s, 1H), 6.35 (dd, J = 11.3,2.4 Hz, 1H), 6.52 (td, J = 8.4, 2.4 Hz, 1H), 6.63 (d, J = 8.2 Hz, 1H),6.77 (d, J = 8.2 Hz, 1H), 6.84 (dd, J = 8.2, 2.3 Hz, 1H), 7.00 (d, J =2.3 Hz, 1H), 7.02-7.05 (m, 1H), 7.19 (d, J = 8.2 Hz, 1H), 7.37-7.47 (m,5H) 5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2,2,2-trichloroethoxycarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 5-8)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.06 (s, 3H), 1.15 (s, 3H), 2.01 (s, 3H),2.06 (s, 3H), 3.74 (s, 3H), 4.61 (d, J = 11.1 Hz, 1H), 5.06 (s, 2H),5.07 (d, J = 11.1 Hz, 1H), 5.40 (s, 1H), 6.06 (s, 1H), 6.36 (dd, J =11.5, 2.4 Hz, 1H), 6.53 (td, J = 8.4, 2.4 Hz, 1H), 6.64 (d, J = 8.2 Hz,1H), 6.78 (d, J = 8.2 Hz, 1H), 6.90 (dd, J = 8.3, 2.2 Hz, 1H), 7.02-7.06(m, 1H), 7.05 (d, J = 2.2 Hz, 1H), 7.23 (d, J = 8.3 Hz, 1H)6-[4-(4-Chlorophenoxycarbonyloxy)-2-methoxyphenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 5-9)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.18 (s, 3H), 2.14 (s, 3H),3.71 (s, 3H), 3.81 (s, 3H), 4.65 (d, J = 11.9 Hz, 1H), 5.25 (d, J = 11.9Hz, 1H), 5.40 (s, 1H), 6.03 (s, 1H), 6.62 (d, J = 8.2 Hz, 1H), 6.76 (d,J = 8.2 Hz, 1H), 6.90 (dd, J = 8.2, 2.3 Hz, 1H), 7.08 (d, J = 9.1 Hz,1H), 7.10 (d, J = 2.3 Hz, 1H), 7.19 (d, J = 8.2 Hz, 1H), 7.31 (d, J =2.7 Hz, 1H), 7.43 (d, J = 8.9 Hz, 2H), 7.55 (d, J = 8.9 Hz, 2H), 7.81(dd, J = 9.1, 2.7 Hz, 1H)6-(2-Methoxy-4-methoxycarbonyloxyphenyl)-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.5-10)  

1H-NMR (500 MHz, DMSO-d₆) δ 1.04 (s, 3H), 1.18 (s, 3H), 2.14 (s, 3H),3.68 (s, 3H), 3.81 (s, 3H), 3.82 (s, 3H), 4.65 (d, J = 12.2 Hz, 1H),5.25 (d, J = 12.2 Hz, 1H), 5.40 (s, 1H), 6.02 (s, 1H), 6.62 (d, J = 8.1Hz, 1H), 6.75 (dd, J = 8.1, 2.2 Hz, 1H), 6.75 (d, J = 8.1 Hz, 1H), 6.93(d, J = 2.2 Hz, 1H), 7.08 (d, J = 9.1 Hz, 1H), 7.14 (d, J = 8.1 Hz, 1H),7.31 (d, J = 2.7 Hz, 1H), 7.81 (dd, J = 9.1, 2.7 Hz, 1H)

Example 65-(5-Fluoro-2-methylphenoxymethyl)-6-(2-methoxy-4-phenylaminocarbonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 6-1)

5-(5-Fluoro-2-methylphenoxymethyl)-6-(4-hydroxy-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Reference Compound No. 3-1, 25.0 mg, 0.058 mmol) was dissolved intetrahydrofuran (0.5 mL), triethylamine (19.3 μL, 0.138 mmol) and phenylisocyanate (9.5 μL, 0.087 mmol) were added thereto, and then the mixturewas stirred at room temperature for 2 hours. The reaction mixture waspurified by silica gel column chromatography (hexane-ethyl acetate) togive the titled compound (27.3 mg) as a colorless amorphous product.(Yield 86%)

¹H-NMR (400 MHz, CDCl₃) δ 1.12 (s, 3H), 1.23 (s, 3H), 2.07 (s, 3H), 2.16(s, 3H), 3.76 (s, 3H), 3.88 (brs, 1H), 4.76 (d, J = 12.0 Hz, 1H), 5.12(d, J = 12.0 Hz, 1H), 5.46 (s, 1H), 6.20 (dd, J = 11.2, 2.4 Hz, 1H),6.42 (td, J = 8.3, 2.4 Hz, 1H), 6.59 (d, J = 8.3 Hz, 1H), 6.82-6.84 (m,2H), 6.90-6.95 (m, 3H), 7.11- 7.14 (m, 1H), 7.25-7.27 (m, 1H), 7.36 (t,J = 8.0 Hz, 2H), 7.47 (d, J = 8.0 Hz, 2H)

6-[4-[N-(2-dimethylaminoethyl)-N-methylaminocarbonyloxy]-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 6-2)

A mixture of5-(5-fluoro-2-methylphenoxymethyl)-6-(4-hydroxy-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Reference Compound No. 3-1, 26.0 mg, 0.0600 mmol),1,1′-carbonyldiimidazole (31.4 mg, 0.194 mmol) and4-dimethylaminopyridine (1.1 mg, 0.0090 mmol) was dissolved in anhydroustetrahydrofuran (0.6 mL), and then the mixture was stirred at roomtemperature for 1 hour. N,N,N′-trimethylethylenediamine (15 μL, 0.12mmol) was added thereto, the mixture was stirred at room temperature for1 hour, and then the mixture was purified by silica gel columnchromatography (hexane-ethyl acetate) to give the titled compound (10.0mg) as a colorless amorphous product. (Yield 30%)

¹H-NMR (500 MHz, DMSO-d₆) δ 1.04 (s, 3H), 1.14 (s, 3H), 2.02 (s, 3H),2.07 (s, 3H), 2.18 (s, 3H), 2.20 (m, 3H), 2.41-2.54 (m, 2H), 2.92- 3.04(m, 3H), 3.30-3.37 (m, 2H), 3.71 (s, 3H), 4.62 (d, J = 12.1 Hz, 1H),5.08 (d, J = 12.1 Hz, 1H), 5.39 (s, 1H), 6.01 (s, 1H), 6.34 (dd, J =11.8, 2.2 Hz, 1H), 6.52 (td, J = 8.2, 2.2 Hz, 1H), 6.63 (d, J = 7.9 Hz,1H), 6.68-6.72 (m, 1H), 6.77 (d, J = 7.9 Hz, 1H), 6.81-6.83 (m, 1H),7.02- 7.05 (m, 1H), 7.15 (d, J = 8.2 Hz, 1H)Using any compounds among Reference Compounds No. 3-1, 3-3 and 3-4, thefollowing Compounds (No. 6-3˜6-41) were obtained by a method similar tothat of Compound No. 1-1, 6-1 or 6-2.

6-[4-(2-Chlorophenylaminocarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No.6-3)  

¹H-NMR (400 MHz, CDCl₃) δ 1.13 (s, 3H), 1.23 (s, 3H), 2.08 (s, 3H), 2.16(s, 3H), 3.77 (s, 3H), 3.88 (br s, 1H), 4.76 (d, J = 12.1 Hz, 1H), 5.12(d, J = 12.1 Hz, 1H), 5.46 (s, 1H), 6.20 (dd, J = 11.2, 2.5 Hz, 1H),6.43 (td, J = 8.4, 2.5 Hz, 1H), 6.59 (d, J = 8.2 Hz, 1H), 6.84 (d, J =2.4 Hz, 1H), 6.85 (dd, J = 8.2, 2.4 Hz, 1H), 6.91 (d, J = 8.2 Hz, 1H),6.92-6.96 (m, 1H), 7.03-7.08 (m, 1H), 7.28 (d, J = 8.2 Hz, 1H),7.29-7.33 (m, 1H), 7.40 (dd, J = 8.1, 1.5 Hz, 1H), 7.50 (br s, 1H), 8.21(d, J = 7.1 Hz, 1H)6-[4-(3-Chlorophenylaminocarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No.6-4)  

¹H-NMR (400 MHz, CDCl₃) δ 1.12 (s, 3H), 1.23 (s, 3H), 2.07 (s, 3H), 2.16(s, 3H), 3.76 (s, 3H), 3.88 (br s, 1H), 4.75 (d, J = 12.0 Hz, 1H), 5.12(d, J = 12.0 Hz, 1H), 5.46 (s, 1H), 6.20 (dd, J = 11.2, 2.4 Hz, 1H),6.42 (td, J = 8.3, 2.4 Hz, 1H), 6.59 (d, J = 8.1 Hz, 1H), 6.81-6.83 (m,2H), 6.91 (d, J = 8.1 Hz, 1H), 6.92-6.95 (m, 1H), 7.09-7.11 (m, 1H),7.25-7.32 (m, 4H), 7.58 (br s, 1H)6-[4-(4-Chlorophenylaminocarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No.6-5)  

¹H-NMR (500 MHz, CDCl₃) δ 1.12 (s, 3H), 1.23 (s, 3H), 2.07 (s, 3H), 2.16(s, 3H), 3.76 (s, 3H), 3.87 (br s, 1H), 4.75 (d, J = 12.2 Hz, 1H), 5.11(d, J = 12.2 Hz, 1H), 5.46 (s, 1H), 6.20 (dd, J = 11.3, 2.4 Hz, 1H),6.42 (td, J = 8.2, 2.4 Hz, 1H), 6.59 (d, J = 8.1 Hz, 1H), 6.81 (d, J =1.9 Hz, 1H), 6.82 (dd, J = 6.9, 1.9 Hz, 1H), 6.90 (d, J = 8.1 Hz, 1H),6.92-6.95 (m, 1H), 7.25-7.27 (m, 2H), 7.32 (d, J = 8.7 Hz, 2H), 7.42 (d,J = 8.7 Hz, 2H) 5-(5-Fluoro-2-methylphenoxymethyl)-6-(2-methoxy-4-propylaminocarbonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 6-6)  

¹H-NMR (400 MHz, CDCl₃) δ 0.99 (t, J = 7.3 Hz, 3H), 1.11 (s, 3H), 1.22(s, 3H), 1.59-1.64 (m, 2H), 2.07 (s, 3H), 2.15 (s, 3H), 3.23-3.28 (m,2H), 3.75 (s, 3H), 3.85 (br s, 1H), 4.75 (d, J = 12.0 Hz, 1H), 5.03 (t,J = 5.9 Hz, 1H), 5.11 (d, J = 12.0 Hz, 1H), 5.44 (s, 1H), 6.19 (dd, J =11.2, 2.4 Hz, 1H), 6.41 (td, J = 8.2, 2.4 Hz, 1H), 6.58 (d, J = 8.1 Hz,1H), 6.75- 6.77 (m, 2H), 6.89 (d, J = 8.1 Hz, 1H), 6.90-6.94 (m, 1H),7.22 (d, J = 8.8 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-pyridin-3-ylaminocarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 6-7)  

¹H-NMR (500 MHz, CDCl₃) δ 1.13 (s, 3H), 1.23 (s, 3H), 2.07 (s, 3H), 2.16(s, 3H), 3.76 (s, 3H), 3.91 (br s, 1H), 4.75 (d, J = 12.1 Hz, 1H), 5.12(d, J = 12.1 Hz, 1H), 5.46 (s, 1H), 6.20 (dd, J = 11.0, 2.5 Hz, 1H),6.43 (td, J = 8.3, 2.5 Hz, 1H), 6.59 (d, J = 8.2 Hz, 1H), 6.82 (d, J =2.3 Hz, 1H), 6.83 (dd, J = 8.1, 2.3 Hz, 1H), 6.90 (d, J = 8.2 Hz, 1H),6.92-6.95 (m, 1H), 7.07 (br s, 1H), 7.27 (d, J = 8.1 Hz, 1H), 7.31 (dd,J = 7.5, 4.9 Hz, 1H), 8.07 (d, J = 7.5 Hz, 1H), 8.38 (dd, J = 4.9, 1.8Hz, 1H), 8.59 (d, J = 1.8 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-(4-dimethylaminophenylaminocarbonyloxy-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 6-8) 

¹H-NMR (400 MHz, Solv. CDCl₃) δ 1.11 (s, 3H), 1.23 (s, 3H), 2.07 (s,3H), 2.16 (s, 3H), 2.93 (s, 6H), 3.76 (s, 3H), 3.86 (br s, 1H), 4.76 (d,J = 12.2 Hz, 1H), 5.12 (d, J = 12.2 Hz, 1H), 5.45 (s, 1H), 6.20 (dd, J =11.1, 2.4 Hz, 1H), 6.42 (td, J = 8.3, 2.4 Hz, 1H), 6.58 (d, J = 8.1 Hz,1H), 6.73-6.75 (m, 3H), 6.81-6.83 (m, 2H), 6.90 (d, J = 8.1 Hz, 1H),6.91-6.95 (m, 1H), 7.24-7.26 (m, 1H), 7.32 (d, J = 7.8 Hz, 2H)6-(4-Benzylaminocarbonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 6-9)  

¹H-NMR (400 MHz, CDCl₃) δ 1.11 (s, 3H), 1.23 (s, 3H), 2.07 (s, 3H), 2.15(s, 3H), 3.75 (s, 3H), 3.87 (br s, 1H), 4.48 (d, J = 5.9 Hz, 2H), 4.75(d, J = 12.1 Hz, 1H), 5.11 (d, J = 12.1 Hz, 1H), 5.34 (t, J = 5.9 Hz,1H), 5.45 (s, 1H), 6.19 (dd, J = 11.2, 2.4 Hz, 1H), 6.41 (td, J = 8.3,2.4 Hz, 1H), 6.58 (d, J = 8.2 Hz, 1H), 6.78-6.79 (m, 2H), 6.90 (d, J =8.2 Hz, 1H), 6.90-6.95 (m, 1H), 7.23 (d, J = 8.8 Hz, 1H), 7.29- 7.38 (m,5H) 6-(4-Cyclohexylaminocarbonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 6-10)  

¹H-NMR (500 MHz, CDCl₃) δ 1.11 (s, 3H), 1.20-1.27 (m, 4H), 1.22 (s, 3H),1.35- 1.43 (m, 2H), 1.74-1.76 (m, 2H), 2.02-2.07 (m, 2H), 2.07 (s, 3H),2.15 (s, 3H), 3.57- 3.59 (m, 1H), 3.74 (s, 3H), 3.86 (br s, 1H), 4.75(d, J = 11.9 Hz, 1H), 4.91 (d, J = 7.9 Hz, 1H), 5.11 (d, J = 11.9 Hz,1H), 5.44 (s, 1H), 6.19 (dd, J = 11.2, 2.4 Hz, 1H), 6.41 (td, J = 8.2,2.4 Hz, 1H), 6.58 (d, J = 8.1 Hz, 1H), 6.75-6.77 (m, 2H), 6.89 (d, J =8.1 Hz, 1H), 6.91-6.94 (m, 1H), 7.21 (d, J = 7.9 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-methoxyphenylaminocarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 6-11)  

¹H-NMR (500 MHz, CDCl₃) δ 1.12 (s, 3H), 1.23 (s, 3H), 2.07 (s, 3H), 2.16(s, 3H), 3.76 (s, 3H), 3.85 (br s, 1H), 3.92 (s, 3H), 4.76 (d, J = 12.2Hz, 1H), 5.12 (d, J = 12.2 Hz, 1H), 5.45 (s, 1H), 6.20 (dd, J = 11.3,2.4 Hz, 1H), 6.42 (td, J = 8.2, 2.4 Hz, 1H), 6.59 (d, J = 7.9 Hz, 1H),6.83-6.85 (m, 2H), 6.90- 6.95 (m, 2H), 6.91 (d, J = 7.9 Hz, 1H), 6.99(td, J = 7.8, 1.3 Hz, 1H), 7.05 (td, J = 7.8, 1.6 Hz, 1H), 7.25-7.27 (m,1H), 7.60 (br s, 1H), 8.12 (br s, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3-methoxyphenylaminocarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 6-12)  

¹H-NMR (400 MHz, CDCl₃) δ 1.12 (s, 3H), 1.23 (s, 3H), 2.07 (s, 3H), 2.16(s, 3H), 3.76 (s, 3H), 3.81 (s, 3H), 3.86 (br s, 1H), 4.75 (d, J = 12.0Hz, 1H), 5.12 (d, J = 12.0 Hz, 1H), 5.45 (s, 1H), 6.20 (dd, J = 11.1,2.5 Hz, 1H), 6.42 (td, J = 8.3, 2.5 Hz, 1H), 6.59 (d, J = 8.1 Hz, 1H),6.68 (dd, J = 7.9, 2.1 Hz, 1H), 6.81-6.84 (m, 2H), 6.90 (d, J = 8.3 Hz,1H), 6.91-6.95 (m, 3H), 7.22-7.28 (m, 3H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-methoxyphenylaminocarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 6-13)  

¹H-NMR (400 MHz, CDCl₃) δ 1.12 (s, 3H), 1.23 (s, 3H), 2.07 (s, 3H), 2.16(s, 3H), 3.76 (s, 3H), 3.81 (s, 3H), 3.86 (br s, 1H), 4.75 (d, J = 12.0Hz, 1H), 5.12 (d, J = 12.0 Hz, 1H), 5.45 (s, 1H), 6.20 (dd, J = 11.2,2.4 Hz, 1H), 6.42 (td, J = 8.3, 2.4 Hz, 1H), 6.59 (d, J = 8.1 Hz, 1H),6.81-6.83 (m, 3H), 6.88-6.95 (m, 3H), 6.91 (d, J = 8.1 Hz, 1H),7.24-7.27 (m, 1H), 7.38 (d, J = 8.3 Hz, 2H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-methoxycarbonylphenylaminocarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 6-14)  

¹H-NMR (400 MHz, CDCl₃) δ 1.12 (s, 3H), 1.23 (s, 3H), 2.08 (s, 3H), 2.16(s, 3H), 3.77 (s, 3H), 3.87 (br s, 1H), 3.91 (s, 3H), 4.75 (d, J = 12.1Hz, 1H), 5.12 (d, J = 12.1 Hz, 1H), 5.46 (s, 1H), 6.20 (dd, J = 11.3,2.4 Hz, 1H), 6.43 (td, J = 8.3, 2.4 Hz, 1H), 6.59 (d, J = 8.1 Hz, 1H),6.82 (d, J = 1.9 Hz, 1H), 6.83 (dd, J = 7.1, 1.9 Hz, 1H), 6.91 (d, J =8.1 Hz, 1H), 6.92-6.96 (m, 1H), 7.12 (br s, 1H), 7.28 (d, J = 7.1 Hz,1H), 7.54 (d, J = 8.8 Hz, 2H), 8.05 (d, J = 8.8 Hz, 2H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-methylphenylaminocarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 6-15)  

¹H-NMR (500 MHz, CDCl₃) δ 1.12 (s, 3H), 1.23 (s, 3H), 2.07 (s, 3H), 2.16(s, 3H), 2.33 (s, 3H), 3.76 (s, 3H), 3.89 (br s, 1H), 4.76 (d, J = 12.1Hz, 1H), 5.12 (d, J = 12.1 Hz, 1H), 5.45 (s, 1H), 6.20 (dd, J = 11.0,2.4 Hz, 1H), 6.42 (td, J = 8.4, 2.4 Hz, 1H), 6.59 (d, J = 7.9 Hz, 1H),6.82-6.83 (m, 2H), 6.87 (br s, 1H), 6.90-6.95 (m, 2H), 7.15 (d, J = 7.9Hz 2H), 7.25 (d, J = 7.0 Hz, 1H), 7.35 (d, J = 7.9 Hz, 2H)6-(4-Dimethylaminocarbonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 6-16)  

¹H-NMR (400 MHz, CDCl₃) δ 1.11 (s, 3H), 1.23 (s, 3H), 2.07 (s, 3H), 2.15(s, 3H), 3.03 (s, 3H), 3.12 (s, 3H), 3.75 (s, 3H), 3.92 (br s, 1H), 4.75(d, J = 12.0 Hz, 1H), 5.11 (d, J = 12.0 Hz, 1H), 5.45 (s, 1H), 6.19 (dd,J = 11.1, 2.5 Hz, 1H), 6.41 (td, J = 8.3, 2.5 Hz, 1H), 6.60 (br s, 1H),6.75 (br s, 2H), 6.89-6.94 (m, 2H), 7.23 (d, J = 8.1 Hz, 1H)6-[4-(4-Cyanophenylaminocarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 6-17)  

¹H-NMR (500 MHz, CDCl₃) δ 1.13 (s, 3H), 1.23 (s, 3H), 2.07 (s, 3H), 2.16(s, 3H), 3.76 (s, 3H), 3.91 (br s, 1H), 4.74 (d, J = 11.9 Hz, 1H), 5.11(d, J = 11.9 Hz, 1H), 5.46 (s, 1H), 6.19 (dd, J = 11.2, 2.5 Hz, 1H),6.43 (td, J = 8.2, 2.5 Hz, 1H), 6.59 (d, J = 8.2 Hz, 1H), 6.81-6.83 (m,2H), 6.90 (d, J = 8.2 Hz, 1H), 6.92-6.95 (m, 1H), 7.16 (br s, 1H), 7.28(d, J = 8.2 Hz, 1H), 7.60 (d, J = 8.9 Hz, 2H), 7.65 (d, J = 8.9 Hz, 2H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(morpholin-4-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 6-18)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.04 (s, 3H), 1.14 (s, 3H), 2.02 (s, 3H),2.07 (s, 3H), 3.42 (br s, 2H), 3.58 (br s, 2H), 3.65 (t, J = 4.8 Hz,4H), 3.71 (s, 3H), 4.61 (d, J = 12.2 Hz, 1H), 5.07 (d, J = 12.2 Hz, 1H),5.39 (s, 1H), 6.02 (s, 1H), 6.34 (dd, J = 11.5, 2.4 Hz, 1H), 6.52 (td, J= 8.4, 2.4 Hz, 1H), 6.63 (d, J = 8.3 Hz, 1H), 6.74 (dd, J = 8.1, 2.3 Hz,1H), 6.78 (d, J = 8.3 Hz, 1H), 6.86 (d, J = 2.3 Hz, 1H), 7.01-7.05 (m,1H), 7.15 (d, J = 8.1 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[4-(4-methylpiperazin-1-ylcarbonyloxy)-2-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 6-19)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.04 (s, 3H), 1.14 (s, 3H), 2.01 (s, 3H),2.07 (s, 3H), 2.22 (s, 3H), 2.33-2.38 (m, 4H), 3.43 (br s, 2H), 3.58 (brs, 2H), 3.71 (s, 3H), 4.61 (d, J = 12.2 Hz, 1H), 5.07 (d, J = 12.2 Hz,1H), 5.39 (s, 1H), 6.02 (s, 1H), 6.34 (dd, J = 11.3, 2.4 Hz, 1H), 6.52(td, J = 8.4, 2.4 Hz, 1H), 6.63 (d, J = 8.2 Hz, 1H), 6.72 (dd, J = 8.1,2.1 Hz, 1H), 6.77 (d, J = 8.2 Hz, 1H), 6.85 (d, J = 2.1 Hz, 1H), 7.02-7.05 (m, 1H), 7.15 (d, J = 8.1 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(piperidin-1-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 6-20)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.04 (s, 3H), 1.14 (s, 3H), 1.55 (br s, 6H),2.02 (s, 3H), 2.07 (s, 3H), 3.41 (br s, 2H), 3.55 (br s, 2H), 3.71 (s,3H), 4.61 (d, J = 12.2 Hz, 1H), 5.08 (d, J = 12.2 Hz, 1H), 5.39 (s, 1H),6.02 (s, 1H), 6.34 (dd, J = 11.2, 2.4 Hz, 1H), 6.52 (td, J = 8.4, 2.4Hz, 1H), 6.63 (d, J = 8.3 Hz, 1H), 6.71 (dd, J = 8.2, 2.2 Hz, 1H), 6.77(d, J = 8.3 Hz, 1H), 6.83 (d, J = 2.2 Hz, 1H), 7.01-7.05 (m, 1H), 7.14(d, J = 8.2 Hz, 1H)6-(4-Isopropylaminocarbonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 6-21)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.03 (s, 3H), 1.13 (d, J = 6.6 Hz, 6H), 1.14(s, 3H), 2.01 (s, 3H), 2.07 (s, 3H), 3.64-3.68 (m, 1H), 3.71 (s, 3H),4.63 (d, J = 12.3 Hz, 1H), 5.08 (d, J = 12.3 Hz, 1H), 5.39 (s, 1H), 6.02(s, 1H), 6.32 (dd, J = 11.6, 2.4 Hz, 1H), 6.52 (td, J = 8.4, 2.4 Hz,1H), 6.62 (d, J = 8.2 Hz, 1H), 6.69 (dd, J = 8.1, 2.2 Hz, 1H), 6.77 (d,J = 8.2 Hz, 1H), 6.80 (d, J = 2.2 Hz, 1H), 7.01-7.05 (m, 1H), 7.13 (d, J= 8.1 Hz, 1H), 7.67 (d, J = 7.8 Hz, 1H)6-(4-t-Butylaminocarbonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 6-22)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.03 (s, 3H), 1.14 (s, 3H), 1.29 (s, 9H),2.01 (s, 3H), 2.07 (s, 3H), 3.72 (s, 3H), 4.63 (d, J = 12.3 Hz, 1H),5.09 (d, J = 12.3 Hz, 1H), 5.39 (s, 1H), 6.02 (s, 1H), 6.32 (dd, J =11.5, 2.5 Hz, 1H), 6.52 (td, J = 8.4, 2.5 Hz, 1H), 6.62 (d, J = 8.2 Hz,1H), 6.67 (dd, J = 8.1, 2.4 Hz, 1H), 6.77 (d, J = 8.2 Hz, 1H), 6.77 (d,J = 2.4 Hz, 1H), 7.01-7.05 (m, 1H), 7.13 (d, J = 8.1 Hz, 1H), 7.56 (s,1H) 5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(N-methyl-N-phenylaminocarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 6-23)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.03 (s, 3H), 1.14 (s, 3H), 2.01 (s, 3H),2.06 (s, 3H), 3.35 (s, 3H), 3.72 (s, 3H), 4.61 (d, J = 12.2 Hz, 1H),5.07 (d, J = 12.2 Hz, 1H), 5.38 (s, 1H), 6.03 (s, 1H), 6.32 (dd, J =11.4, 2.4 Hz, 1H), 6.51 (td, J = 8.4, 2.4 Hz, 1H), 6.62 (d, J = 8.2 Hz,1H), 6.73-6.96 (m, 2H), 6.77 (d, J = 8.2 Hz, 1H), 7.01- 7.05 (m, 1H),7.15 (d, J = 8.3 Hz, 1H), 7.28 (t, J = 7.8 Hz, 1H), 7.42 (t, J = 7.8 Hz,2H), 7.48 (d, J = 7.8 Hz, 2H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[4-(4-hydroxypiperidin-1-ylcarbonyloxy)-2-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 6-24)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.04 (s, 3H), 1.14 (s, 3H), 1.40 (br s, 2H),1.78 (br s, 2H), 2.02 (s, 3H), 2.07 (s, 3H), 3.14 (br s, 1H), 3.30- 3.33(m, 1H), 3.71 (s, 3H), 3.71 (br s, 2H), 3.86 (br s, 1H), 4.61 (d, J =12.5 Hz, 1H), 4.80 (d, J = 4.2 Hz, 1H), 5.08 (d, J = 12.5 Hz, 1H), 5.39(s, 1H), 6.02 (s, 1H), 6.34 (dd, J = 11.4, 2.5 Hz, 1H), 6.52 (td, J =8.5, 2.5 Hz, 1H), 6.62 (d, J = 8.3 Hz, 1H), 6.71 (dd, J = 8.2, 2.2 Hz,1H), 6.77 (d, J = 8.3 Hz, 1H), 6.84 (d, J = 2.2 Hz, 1H), 7.01-7.05 (m,1H), 7.14 (d, J = 8.2 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(thiomorpholin-4-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline (CompoundNo. 6-25)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.05 (s, 3H), 1.15 (s, 3H), 2.02 (s, 3H),2.07 (s, 3H), 2.67-2.76 (m, 4H), 3.65- 3.73 (m, 2H), 3.72 (s, 3H),3.81-3.87 (m, 2H), 4.61 (d, J = 12.2 Hz, 1H), 5.08 (d, J = 12.2 Hz, 1H),5.39 (s, 1H), 6.03 (s, 1H), 6.34 (dd, J = 11.5, 2.5 Hz, 1H), 6.53 (td, J= 8.4, 2.5 Hz, 1H), 6.63 (d, J = 8.3 Hz, 1H), 6.74 (dd, J = 8.2, 2.3 Hz,1H), 6.78 (dd, J = 8.3 Hz, 1H), 6.88 (d, J = 2.3 Hz, 1H), 7.02-7.05 (m,1H), 7.16 (d, J = 8.2 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(N-methyl-N-propylaminocarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 6-26)  

¹H-NMR (400 MHz, CDCl₃) δ 0.88-1.01 (m, 3H), 1.11 (s, 3H), 1.22 (s, 3H),1.64- 1.73 (m, 2H), 2.07 (s, 3H), 2.15 (s, 3H), 3.01-3.09 (m, 3H),3.32-3.42 (m, 2H), 3.75 (s, 3H), 4.75 (d, J = 12.1 Hz, 1H), 5.11 (d, J =12.1 Hz, 1H), 5.44 (s, 1H), 6.19 (dd, J = 11.1, 2.3 Hz, 1H), 6.41 (td, J= 8.3, 2.3 Hz, 1H), 6.58 (d, J = 8.6 Hz, 1H), 6.72- 6.77 (m, 2H),6.89-6.94 (m, 2H), 7.23 (d, J = 8.6 Hz, 1H)5-(5-Fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(piperazin-1-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinolinemonohydrochloride (Compound No. 6-27)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.09 (s, 3H), 1.20 (s, 3H), 2.01 (s, 3H),2.09 (s, 3H), 3.19 (br s, 4H), 3.67 (br s, 2H), 3.73 (s, 3H), 3.82 (brs, 2H), 4.62-5.51 (br s, 1H), 4.63 (d, J = 12.2 Hz, 1H), 5.10 (d, J =12.2 Hz, 1H), 5.51 (s, 1H), 6.34 (dd, J = 11.5, 2.2 Hz, 1H), 6.54 (td, J= 8.4, 2.4 Hz, 1H), 6.79 (dd, J = 8.2, 2.2 Hz, 1H), 6.77-6.91 (m, 2H),6.91 (dd, J = 2.2 Hz, 1H), 7.02-7.06 (m, 1H), 7.19 (d, J = 8.2 Hz, 1H),9.30 (br s, 1H), 9.37 (br s, 1H)6-[2-Methoxy-4-(morpholin-4-ylcarbonyloxy)phenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 6-28)  

¹H-NMR (500 MHz, DMSO-d₆) δ 1.03 (s, 3H), 1.18 (s, 3H), 2.14 (s, 3H),3.41-3.64 (m, 8H), 3.68 (s, 3H), 3.82 (s, 3H), 4.66 (d, J = 11.9 Hz,1H), 5.25 (d, J = 11.9 Hz, 1H), 5.39 (s, 1H), 6.01 (s, 1H), 6.61 (d, J =8.2 Hz, 1H), 6.66 (dd, J = 8.2, 2.3 Hz, 1H), 6.75 (d, J = 8.2 Hz, 1H),6.81 (d, J = 2.3 Hz, 1H), 7.08 (d, J = 9.0 Hz, 1H), 7.12 (d, J = 8.2 Hz,1H), 7.30 (d, J = 2.7 Hz, 1H), 7.81 (dd, J = 9.0, 2.7 Hz, 1H)6-[4-[N-(2-Dimethylaminoethyl)-N-methylaminocarbonyloxy]-2-methoxyphenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 6-29)  

¹H-NMR (400 MHz, DMSO-d₆) δ 1.02 (s, 3H), 1.18 (s, 3H), 2.14 (s, 3H),2.17 (s, 6H), 2.32-2.68 (m, 2H), 2.90, 3.02 (s, 3H), 3.31-3.45 (m, 2H),3.68 (s, 3H), 3.82 (s, 3H), 4.66 (d, J = 12.1 Hz, 1H), 5.26 (d, J = 12.1Hz, 1H), 5.39 (s, 1H), 6.01 (s, 1H), 6.60-6.65 (m, 1H), 6.61 (d, J = 8.3Hz, 1H), 6.74-6.78 (m, 1H), 6.75 (d, J = 8.3 Hz, 1H), 7.07-7.12 (m, 1H),7.08 (d, J = 8.9 Hz, 1H), 7.30 (d, J = 2.7 Hz, 1H), 7.80 (dd, J = 8.9,2.7 Hz, 1H) 6-[2-Methoxy-4-(morpholin-4-ylcarbonyloxy)phenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline(Compound No. 6-30)  

¹H-NMR (500 MHz, DMSO-d₆) δ 0.89 (s, 3H), 1.18 (s, 3H), 2.12 (s, 3H),2.18 (s, 3H), 3.38-3.48 (m, 2H), 3.51- 3.63 (m, 2H), 3.63-3.67 (m, 4H),3.73 (s, 3H), 4.77 (d, J = 12.5 Hz, 1H), 5.31 (d, J = 12.5 Hz, 1H), 5.40(s, 1H), 6.02 (s, 1H), 6.62 (d, J = 8.2 Hz, 1H), 6.77 (dd, J = 8.2, 2.0Hz, 1H), 6.79 (d, J = 8.2 Hz, 1H), 6.87 (d, J = 2.0 Hz, 1H), 7.14 (d, J= 2.1 Hz, 1H), 7.25 (d, J = 8.2 Hz, 1H), 7.33 (d, J = 8.2 Hz, 1H), 7.63(dd, J = 8.2, 2.1 Hz, 1H)6-(4-Dimethylaminocarbonyloxy-2-methoxyphenyl)-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No.6-31)  

¹H-NMR (500 MHz, DMSO-d₆) δ 0.89 (s, 3H), 1.18 (s, 3H), 2.12 (s, 3H),2.18 (s, 3H), 2.92 (s, 3H), 3.05 (s, 3H), 3.73 (s, 3H), 4.78 (d, J =12.5 Hz, 1H), 5.31 (d, J = 12.5 Hz, 1H), 5.39 (s, 1H), 6.02 (s, 1H),6.62 (d, J = 8.2 Hz, 1H), 6.74 (dd, J = 8.2, 2.3 Hz, 1H), 6.79 (d, J =8.2 Hz, 1H), 6.84 (d, J = 2.3 Hz, 1H), 7.14 (d, J = 2.1 Hz, 1H), 7.24(d, J = 8.2 Hz, 1H), 7.33 (d, J = 8.2 Hz, 1H), 7.63 (dd, J = 8.2, 2.1Hz, 1H) 6-[4-[N-(2-Dimethylaminoethyl)-N-ethylaminocarbonyloxy]-2-methoxyphenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 6-32)  

¹H-NMR (500 MHz, CDCl₃) δ 0.99 (s, 3H), 1.21-1.28 (m, 3H), 1.25 (s, 3H),2.26 (s, 3H), 2.29 (s, 6H), 2.52- 2.57 (m, 2H), 3.41-3.50 (m, 4H), 3.76(s, 3H), 3.79 (s, 1H), 3.83 (s, 3H), 4.86 (d, J = 12.7 Hz, 1H), 5.38 (d,J = 12.7 Hz, 1H), 5.44 (s, 1H), 6.55 (d, J = 8.1 Hz, 1H), 6.73- 6.75 (m,1H), 6.75 (d, J = 2.1 Hz, 1H), 6.76 (d, J = 8.9 Hz, 1H), 6.86 (d, J =8.1 Hz, 1H), 7.26-7.28 (m, 1H), 7.28 (d, J = 2.6 Hz, 1H), 7.76 (dd, J =8.9, 2.6 Hz, 1H)6-[4-[N-(2-Dimethylaminoethyl)-N-methylaminocarbonyloxy]-2-methoxyphenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 6-33)  

¹H-NMR (500 MHz, CDCl₃) δ 1.00 (s, 3H), 1.05 (t, J = 7.2 Hz, 6H), 1.26(s, 3H), 2.26 (s, 3H), 2.58 (q, J = 7.2 Hz, 4H), 2.66-2.71 (m, 2H),3.04, 3.13 (s, 3H), 3.41- 3.50 (m, 2H), 3.75 (s, 3H), 3.83 (s, 3H),4.85-4.89 (m, 1H), 5.37-5.40 (m, 1H), 5.44 (s, 1H), 6.55 (d, J = 8.1 Hz,1H), 6.72-6.75 (m, 1H), 6.72 (d, J = 2.1 Hz, 1H), 6.76 (d, J = 8.9 Hz,1H), 6.87 (d, J = 8.1 Hz, 1H), 7.25-7.29 (m, 2H), 7.76 (dd, J = 8.9, 2.7Hz, 1H) 6-[4-[N-(3-Dimethylaminopropyl)-N-methylaminocarbonyloxy]-2-methoxyphenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 6-34)  

¹H-NMR (500 MHz, CDCl₃) δ 1.00 (s, 3H), 1.26 (s, 3H), 1.78-1.85 (m, 2H),2.24 (s, 6H), 2.26 (s, 3H), 2.31- 2.36 (m, 2H), 3.02, 3.09 (s, 3H),3.38-3.48 (m, 2H), 3.75 (s, 3H), 3.80 (s, 1H), 3.83 (s, 3H), 4.87 (d, J= 12.4 Hz, 1H), 5.38 (d, J = 12.4 Hz, 1H), 5.44 (s, 1H), 6.55 (d, J =8.2 Hz, 1H), 6.71-6.75 (m, 2H), 6.76 (d, J = 9.1 Hz, 1H), 6.87 (d, J =8.2 Hz, 1H), 7.26-7.30 (m, 2H), 7.77 (dd, J = 9.1, 2.6 Hz, 1H)6-[4-[N-(2-Dimethylaminoethyl)-N-methylaminocarbonyloxy]-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 6-35)  

¹H-NMR (400 MHz, CDCl₃) δ 1.06 (t, J = 7.2 Hz, 6H), 1.11 (s, 3H), 1.22(s, 3H), 2.07 (s, 3H), 2.15 (s, 3H), 2.59 (q, J = 7.2 Hz, 4H), 2.66-2.73 (m, 2H), 3.05, 3.14 (s, 3H), 3.42-3.52 (m, 2H), 3.75 (s, 3H), 4.76(d, J = 11.5 Hz, 1H), 5.11 (d, J = 11.5 Hz, 1H), 5.44 (s, 1H), 6.19 (dd,J = 11.2, 2.3 Hz, 1H), 6.41 (td, J = 8.3, 2.3 Hz, 1H), 6.57 (d, J = 8.1Hz, 1H), 6.73-6.77 (m, 2H), 6.88-6.94 (m, 2H), 7.22 (d, J = 8.3 Hz, 1H)6-[4-[N-(3-Dimethylaminopropyl)-N-methylaminocarbonyloxy]-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 6-36)  

¹H-NMR (400 MHz, CDCl₃) δ 1.11 (s, 3H), 1.22 (s, 3H), 1.77-1.88 (m, 2H),2.07 (s, 3H), 2.15 (s, 3H), 2.25 (s, 6H), 2.32-2.39 (m, 2H), 3.03, 3.11(s, 3H), 3.38-3.51 (m, 2H), 3.75 (s, 3H), 4.75 (d, J = 12.1 Hz, 1H),5.11 (d, J = 12.1 Hz, 1H), 5.44 (s, 1H), 6.19 (dd, J = 11.2, 2.5 Hz,1H), 6.41 (td, J = 8.2, 2.5 Hz, 1H), 6.58 (d, J = 8.1 Hz, 1H), 6.72-6.77(m, 2H), 6.88-6.95 (m, 2H), 7.22 (d, J = 8.8 Hz, 1H)6-[4-[N-Benzyl-N-(2-dimethyl-aminoethyl)aminocarbonyloxy]-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 6-37)  

¹H-NMR (400 MHz, CDCl₃) δ 1.13 (s, 3H), 1.25 (s, 3H), 2.07 (s, 3H), 2.16(s, 3H), 2.85 (s, 6H), 3.13-3.23 (m, 2H), 3.77 (s, 3H), 3.81- 3.96 (m,2H), 4.66-4.85 (m, 3H), 5.11 (d, J = 12.2 Hz, 1H), 5.47 (s, 1H), 6.18(dd, J = 11.1, 2.4 Hz, 1H), 6.42 (td, J = 8.3, 2.4 Hz, 1H), 6.65 (d, J =7.8 Hz, 1H), 6.79 (dd, J = 8.1, 1.7 Hz, 1H), 6.88- 6.96 (m, 3H), 7.25(d, J = 8.1 Hz, 1H), 7.32-7.52 (m, 5H)6-[4-[N-(2-Dimethylaminoethyl)-N-(pyridin-3-ylmethyl)aminocarbonyloxy]-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 6-38)  

¹H-NMR (500 MHz, CDCl₃) δ 1.11 (s, 3H), 1.23 (s, 3H), 2.07 (s, 3H), 2.15(s, 3H), 2.28 (s, 3H), 2.30-2.34 (m, 3H), 2.54-2.62 (m, 2H), 3.50-3.54(m, 2H), 3.73-3.77 (m, 3H), 4.64 (s, 1H), 4.72- 4.77 (m, 2H), 5.08-5.13(m, 1H), 5.44 (s, 1H), 6.17-6.21 (m, 1H), 6.41 (td, J = 8.2, 2.4 Hz,1H), 6.58 (d, J = 7.9 Hz, 1H), 6.71-6.78 (m, 2H), 6.86-6.95 (m, 2H),7.22-7.35 (m, 2H), 7.72-7.76 (m, 1H), 8.56-8.65 (m, 2H)6-[4-[N-Benzyl-N-(2-dimethylaminoethyl)aminocarbonyloxy]-2-methoxyphenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 6-39)  

¹H-NMR (500 MHz, CDCl₃) δ 0.99 (s, 3H), 1.26 (s, 3H), 2.24 (s, 3H), 2.26(s, 6H), 2.50-2.51 (m, 2H), 3.46 (t, J = 7.0 Hz, 2H), 3.74, 3.77 (s,3H), 3.82, 3.83 (s, 3H), 4.61, 4.70 (s, 2H), 4.84- 4.89 (m, 1H),5.36-5.41 (m, 1H), 5.44 (s, 1H), 6.55 (d, J = 7.6 Hz, 1H), 6.67-6.88 (m,4H), 7.27-7.38 (m, 7H), 7.76 (d, J = 8.9 Hz, 1H)6-[4-[N-(2-Dimethylaminoethyl)-N-(pyridin-3-ylmethyl)aminocarbonyloxy]-2-methoxyphenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 6-40)  

¹H-NMR (500 MHz, CDCl₃) δ 1.00 (s, 3H), 1.26 (s, 3H), 2.25 (s, 6H), 2.26(s, 3H), 2.52 (t, J = 6.7 Hz, 2H), 3.48 (t, J = 6.7 Hz, 2H), 3.74, 3.77(s, 3H), 3.83 (s, 3H), 3.83-3.88 (m, 1H), 4.63, 4.72 (s, 2H), 4.83-4.88(m, 1H), 5.36-5.40 (m, 1H), 5.45 (s, 1H), 6.55 (d, J = 8.2 Hz, 1H),6.67-6.88 (m, 3H), 6.76 (d, J = 9.2 Hz, 1H), 7.26- 7.31 (m, 3H),7.72-7.77 (m, 1H), 7.76 (d, J = 8.9 Hz, 1H), 8.57-8.62 (m, 2H)6-[4-[N-(2-Dimethylaminoethyl)-N-ethylaminocarbonyloxy]-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 6-41)  

¹H-NMR (500 MHz, CDCl₃) δ 1.10 (s, 3H), 1.22 (s, 3H), 1.26 (t, J = 7.4Hz, 3H), 2.07 (s, 3H), 2.15 (s, 3H), 2.30 (s, 6H), 2.52-2.59 (m, 2H),3.40-3.52 (m, 4H), 3.75 (s, 3H), 4.76 (d, J = 11.9 Hz, 1H), 5.11 (d, J =11.9 Hz, 1H), 5.44 (s, 1H), 6.19 (dd, J = 11.3, 2.4 Hz, 1H), 6.41 (td, J= 8.4, 2.4 Hz, 1H), 6.57 (d, J = 8.2 Hz, 1H), 6.74- 6.77 (m, 2H),6.87-6.94 (m, 2H), 7.22 (d, J = 8.6 Hz, 1H)

PREPARATION EXAMPLES

Hereinafter, typical preparation examples of the present compound areshown.

1) Tablet (in 150 mg)

Present compound 1 mg Lactose 100 mg Cornstarch 40 mg Carboxymethylcellulose calcium 4.5 mg Hydroxypropyl cellulose 4 mg Magnesium stearate0.5 mg

A tablet of the above-mentioned formulation is coated with 3 mg of acoating agent (for example, a coating agent which is used conventionallysuch as hydroxypropylmethyl cellulose, macrogol or a silicone resin),whereby an objective tablet can be obtained. In addition, a desiredtablet can be obtained by appropriately changing the kind and/or amountof the present compound and additives.

2) Capsule (in 150 mg)

Present compound 5 mg Lactose 135 mg Carboxymethyl cellulose calcium 4.5mg Hydroxypropyl cellulose 4 mg Magnesium stearate 1.5 mg

A desired capsule can be obtained by appropriately changing the kindand/or amount of the present compound and additives.

3) Eye Drop (in 100 mL)

Present compound 100 mg Sodium chloride 900 mg Polysorbate 80 500 mgSodium hydroxide q.s. Hydrochloric acid q.s. Sterile purified water q.s.

A desired eye drop can be obtained by appropriately changing the kindand/or amount of the present compound and additives.

[Pharmacological Test]

1. Evaluation Test for Binding Activity to Glucocorticoid Receptor(Hereinafter Referred to as “GR”)

In order to evaluate a binding activity to GR, a receptor competitorassay was carried out by a fluorescence polarization method. In theassay, a GR competitor assay kit (manufactured by Invitrogen, cat No.P2816) was used, and a procedure was carried out according to theprotocol attached to the kit. Hereinafter, the specific method will bedescribed.

(Preparation of Reagents)

GR screening buffer: A buffer containing 10 mM potassium phosphate (pH7.4), 20 mM sodium molybdate (Na₂MoO₄), 0.1 mM ethylene diaminetetraacetic acid (EDTA), 5 mM dithiothreitol (DTT), 0.1 mM stabilizingpeptide and 2% dimethylsulfoxide was prepared.

4×GS1 solution: Fluormone™ GS1, which is a fluorescent glucocorticoidligand, was diluted with GR screening buffer, whereby a 4 nM solutionwas prepared.

4×GR solution: Recombinant human GR was diluted with GR screeningbuffer, whereby a 16 nM solution was prepared.

(Preparation of Test Compound Solution)

After a test compound was dissolved in dimethylsulfoxide, the resultingsolution was diluted with GR screening buffer, whereby a 20 μM testcompound solution was prepared.

(Test Method and Measurement Method)

1) The test compound solution was added in an amount of 10 μL into eachwell of a 384-well plate, and then, 4×GS1 solution and 4×GR solutionwere added in an amount of 5 μL into each well, respectively.

2) The plate was incubated in a dark place at room temperature for 2 to4 hours.

3) By using a multimode plate reader, Analyst™ HT (manufactured by LJLBiosystems), fluorescence polarization of each well was measured. As theblank, a well containing GR screening buffer in place of the testcompound and 4×GS1 solution was used.

4) The same procedure as that in the above 1) to 3) was carried outexcept that GR screening buffer was used in place of the test compoundsolution, and the obtained result was taken as the negative control.

5) The same procedure as that in the above 1) to 3) was carried outexcept that 2 mM dexamethasone was used in place of the test compoundsolution, and the obtained result was taken as the positive control.

(Calculation Equation of GR Binding Ratio)

A GR binding ratio (%) was calculated from the following equation.GR binding ratio (%)=100×[1−(fluorescence polarization of test compoundsolution−fluorescence polarization of positive controlsolution)/(fluorescence polarization of negative controlsolution−fluorescence polarization of positive control solution)](Test Results and Discussion)

As an example of the test results, the GR binding ratios (%) of the testcompounds (Compound 1-1, Compound 1-2, Compound 1-6, Compound 1-7,Compound 1-8, Compound 1-11, Compound 1-12, Compound 1-13, Compound1-14, Compound 1-16, Compound 1-17, Compound 1-18, Compound 1-19,Compound 1-20, Compound 1-21, Compound 1-27, Compound 1-31, Compound1-33, Compound 1-34, Compound 1-35, Compound 1-40, Compound 1-43,Compound 1-44, Compound 1-45, Compound 1-50, Compound 1-51, Compound1-52, Compound 1-53, Compound 1-54, Compound 1-55, Compound 1-56,Compound 1-58, Compound 1-59, Compound 1-60, Compound 1-62, Compound1-63, Compound 1-64, Compound 1-67, Compound 1-68, Compound 1-69,Compound 1-70, Compound 1-71, Compound 1-72, Compound 1-78, Compound1-86, Compound 1-90, Compound 1-91, Compound 1-93, Compound 1-94,Compound 1-95, Compound 1-98, Compound 1-101, Compound 1-102, Compound1-115, Compound 1-121, Compound 1-122, Compound 1-125, Compound 3-1,Compound 4-11, Compound 4-12, Compound 4-13, Compound 4-14, Compound4-18, Compound 4-19, Compound 4-20, Compound 4-23, Compound 4-25,Compound 4-26, Compound 4-27, Compound 4-28, Compound 4-29, Compound4-30, Compound 5-5, Compound 6-3, Compound 6-12, Compound 6-13, Compound6-14, Compound 6-16, Compound 6-17, Compound 6-18, Compound 6-21,Compound 6-28, Compound 6-30, Compound 6-31, Compound 6-37, Compound6-38, Compound 6-41) are shown in Table I.

TABLE I GR Binding Test compound ratio (%) Compound 1-1 94 Compound 1-2100 Compound 1-6 100 Compound 1-7 100 Compound 1-8 100 Compound 1-11 100Compound 1-12 100 Compound 1-13 100 Compound 1-14 100 Compound 1-16 100Compound 1-17 100 Compound 1-18 100 Compound 1-19 100 Compound 1-20 100Compound 1-21 100 Compound 1-27 84 Compound 1-31 100 Compound 1-33 89Compound 1-34 100 Compound 1-35 100 Compound 1-40 100 Compound 1-43 100Compound 1-44 100 Compound 1-45 95 Compound 1-50 97 Compound 1-51 91Compound 1-52 96 Compound 1-53 100 Compound 1-54 100 Compound 1-55 100Compound 1-56 100 Compound 1-58 100 Compound 1-59 100 Compound 1-60 100Compound 1-62 100 Compound 1-63 100 Compound 1-64 100 Compound 1-67 100Compound 1-68 100 Compound 1-69 100 Compound 1-70 100 Compound 1-71 100Compound 1-72 98 Compound 1-78 100 Compound 1-86 91 Compound 1-90 95Compound 1-91 96 Compound 1-93 92 Compound 1-94 100 Compound 1-95 93Compound 1-98 100 Compound 1-101 99 Compound 1-102 100 Compound 1-115 97Compound 1-121 100 Compound 1-122 100 Compound 1-125 100 Compound 3-1100 Compound 4-11 100 Compound 4-12 92 Compound 4-13 89 Compound 4-14 90Compound 4-18 99 Compound 4-19 98 Compound 4-20 100 Compound 4-23 100Compound 4-25 100 Compound 4-26 100 Compound 4-27 100 Compound 4-28 100Compound 4-29 100 Compound 4-30 100 Compound 5-5 93 Compound 6-3 98Compound 6-12 98 Compound 6-13 100 Compound 6-14 88 Compound 6-16 100Compound 6-17 90 Compound 6-18 100 Compound 6-21 92 Compound 6-28 100Compound 6-30 100 Compound 6-31 100 Compound 6-37 99 Compound 6-38 100Compound 6-41 87

Incidentally, in the case where the GR binding ratio of the testcompound is 100% or more, the GR binding ratio is indicated by 100%.

As is apparent from Table I, the present compound showed an excellent GRbinding activity. Accordingly, the present compound can be used as a GRmodulator, and is useful for a preventive or therapeutic agentparticularly for GR-related diseases, that is, metabolic disorders,inflammatory diseases, autoimmune diseases, allergic diseases, centralnervous system diseases, cardiovascular diseases, homeostasis-relateddiseases, glaucoma and the like.

The invention claimed is:
 1. A method for treating a disease related tothe glucocorticoid receptor selected from the group consisting ofobesity, enteritis, asthma, atopic dermatitis, allergic rhinitis,Alzheimer's disease, hypertension, hypercalcemia, hyperinsulinemia,hyperlipidemia, a homeostasis-related disease causing an abnormality ofneuro-immune-endocrine balance and glaucoma, the method comprisingadministering a pharmacologically effective amount of a compoundrepresented by the following formula (1) or a pharmaceuticallyacceptable salt thereof as an active ingredient to a patient:

wherein R¹ represents a hydrogen atom or a lower alkyl group; R²represents a hydrogen atom or a lower alkyl group; R³ and R⁴ are thesame or different and represent a hydrogen atom or a lower alkyl group;R⁵ represents a hydrogen atom or a lower alkyl group; R⁶ represents ahalogen atom, a lower alkyl group, a hydroxy group, a lower alkoxygroup, a nitro group or a cyano group; X represents —C(O)—, —C(O)NR⁸—,—S(O)— or —S(O)₂—; R⁷ and/or R⁸ are the same or different and representa hydrogen atom, a lower alkyl group which optionally has a substituent,a lower alkenyl group which optionally has a substituent, a loweralkynyl group which optionally has a substituent, a lower cycloalkylgroup which optionally has a substituent, an aryl group which optionallyhas a substituent, a heterocyclic group which optionally has asubstituent, a lower alkoxy group which optionally has a substituent, alower alkenyloxy group which optionally has a substituent, a loweralkynyloxy group which optionally has a substituent, a lowercycloalkyloxy group which optionally has a substituent, an aryloxy groupwhich optionally has a substituent or a heterocyclic oxy group whichoptionally has a substituent; Y represents a lower alkylene group; Zrepresents a chalcogen atom; p represents 0, 1, 2 or 3, in the casewhere p is 2 or 3, each R⁶ are the same or different.
 2. The methodaccording to claim 1, wherein in the formula (1), R¹ represents ahydrogen atom or a lower alkyl group; R² represents a hydrogen atom or alower alkyl group; R³ and R⁴ are the same or different and represent ahydrogen atom or a lower alkyl group; R⁵ represents a hydrogen atom or alower alkyl group; R⁶ represents a halogen atom, a lower alkyl group, ahydroxy group, a lower alkoxy group, a nitro group or a cyano group; Xrepresents —CO—, —C(O)NR⁸—, —S(O)— or —S(O)₂—; R⁷ and/or R⁸ are the sameor different and represent a hydrogen atom, a lower alkyl group, a loweralkenyl group, a lower alkynyl group, a lower cycloalkyl group, an arylgroup, a heterocyclic group, a lower alkoxy group, a lower alkenyloxygroup, a lower alkynyloxy group, a lower cycloalkyloxy group, an aryloxygroup or a heterocyclic oxy group; in the case where R⁷ and/or R⁸ is alower alkyl group, a lower alkenyl group, a lower alkynyl group, a loweralkoxy group, a lower alkenyloxy group or a lower alkynyloxy group, thelower alkyl group, the lower alkenyl group, the lower alkynyl group, thelower alkoxy group, the lower alkenyloxy group or the lower alkynyloxygroup optionally has one or a plurality of substituents selected fromthe group consisting of a halogen atom, a lower cycloalkyl group, anaryl group, a heterocyclic group, a hydroxy group, a lower alkoxy group,a lower alkenyloxy group, a lower alkynyloxy group, a lowercycloalkyloxy group, an aryloxy group, a heterocyclic oxy group and—NR^(a)R^(b); in the case where R⁷ and/or R⁸ is a lower cycloalkylgroup, an aryl group, a heterocyclic group, a lower cycloalkyloxy group,an aryloxy group or a heterocyclic oxy group, the lower cycloalkylgroup, the aryl group, the heterocyclic group, the lower cycloalkyloxygroup, the aryloxy group or the heterocyclic oxy group optionally hasone or a plurality of substituents selected from the group consisting ofa halogen atom, a lower alkyl group, a halogenated lower alkyl group, anaryl group, lower alkenyl group, a lower alkynyl group, a lowercycloalkyl group, an aryl group, a heterocyclic group, a hydroxy group,a lower alkoxy group, a halogenated lower alkoxy group, a loweralkenyloxy group, a lower alkynyloxy group, a lower cycloalkyloxy group,an aryloxy group, a heterocyclic oxy group, a mercapto group, a loweralkyl thio group, a lower alkenylthio group, a lower alkynylthio group,a lower cycloalkylthio group, an arylthio group, a heterocyclic thiogroup, a lower alkylcarbonyl group, an arylcarbonyl group, a loweralkoxycarbonyl group, an aryloxycarbonyl group, a lower alkylcarbonyloxygroup, an arylcarbonyloxy group, —NR^(a)R^(b), a nitro group and a cyanogroup; R^(a) and R^(b) are the same or different and represent ahydrogen atom, a lower alkyl group, a lower alkenyl group, a loweralkynyl group, a lower cycloalkyl group, an aryl group, a heterocyclicgroup, a lower alkoxycarbonyl group or an aryloxycarbonyl group; Yrepresents a lower alkylene group; Z represents a chalcogen atom; prepresents 0, 1, 2 or 3, in the case where p is 2 or 3, each R⁶ is thesame or different.
 3. The method according to claim 1, wherein in theformula (1), R¹ represents a hydrogen atom or a lower alkyl group; R²represents a hydrogen atom or a lower alkyl group; R³ and R⁴ are thesame or different and represent a hydrogen atom or a lower alkyl group;R⁵ represents a hydrogen atom or a lower alkyl group; R⁶ represents ahalogen atom, a lower alkyl group, a hydroxy group, a lower alkoxy groupor a nitro group; X represents —CO—, —C(O)NR⁸—, —S(O)— or —S(O)₂—; R⁷and/or R⁸ are the same or different and represent a hydrogen atom, alower alkyl group, a lower alkenyl group, a lower alkynyl group, a lowercycloalkyl group, an aryl group, a heterocyclic group, a lower alkoxygroup, a lower alkenyloxy group, a lower alkynyloxy group, a lowercycloalkyloxy group, an aryloxy group or a heterocyclic oxy group; inthe case where R⁷ and/or R⁸ is a lower alkyl group, a lower alkenylgroup, a lower alkynyl group, a lower alkoxy group, a lower alkenyloxygroup or a lower alkynyloxy group, the lower alkyl group, the loweralkenyl group, the lower alkynyl group, the lower alkoxy group, thelower alkenyloxy group or the lower alkynyloxy group optionally has oneor a plurality of substituents selected from the group consisting of ahalogen atom, a lower cycloalkyl group, an aryl group, a heterocyclicgroup, a hydroxy group, a lower alkoxy group, a lower cycloalkyloxygroup, an aryloxy group, a heterocyclic oxy group and —NR^(a)R^(b); inthe case where R⁷ and/or R⁸ is a lower cycloalkyl group, an aryl group,a heterocyclic group, a lower cycloalkyloxy group, an aryloxy group or aheterocyclic oxy group, the lower cycloalkyl group, the aryl group, theheterocyclic group, the lower cycloalkyloxy group, the aryloxy group orthe heterocyclic oxy group optionally has one or a plurality ofsubstituents selected from the group consisting of a halogen atom, alower alkyl group, a halogenated lower alkyl group, a lower cycloalkylgroup, an aryl group, a hydroxy group, a lower alkoxy group, ahalogenated lower alkoxy group, a cycloalkyloxy group, an aryloxy group,a mercapto group, a lower alkylthio group, a lower cycloalkylthio group,an arylthio group, a heterocyclic thio group, a lower alkylcarbonylgroup, an arylcarbonyl group, a lower alkoxycarbonyl group, anaryloxycarbonyl group, a lower alkylcarbonyloxy group, anarylcarbonyloxy group, —NR^(a)R^(b), a nitro group and a cyano group;R^(a) and R^(b) are the same or different and represent a hydrogen atom,a lower alkyl group or a lower alkoxycarbonyl group; Y represents alower alkylene group; Z represents an oxygen atom or a sulfur atom; prepresents 0, 1, 2 or 3, in the case where p is 2 or 3, each R⁶ is thesame or different.
 4. The method according to claim 1, wherein in theformula (1), R¹ represents a lower alkyl group; R² represents a hydrogenatom; R³ and R⁴ represent a lower alkyl group; R⁵ represents a loweralkyl group; R⁶ represents a halogen atom, a lower alkyl group, ahydroxy group, a lower alkoxy group or a nitro group; X represents —CO—,—C(O)NR⁸— or —S(O)₂—; R⁷ represents a lower alkyl group, a lower alkenylgroup, a lower cycloalkyl group, an aryl group, a heterocyclic group, alower alkoxy group or an aryloxy group; in the case where R⁷ is a loweralkyl group or a lower alkoxy group, the lower alkyl group or the loweralkoxy group optionally has one or a plurality of substituents selectedfrom the group consisting of a halogen atom, an aryl group, aheterocyclic group, a lower alkoxy group and —NR^(a)R^(b); in the casewhere R⁷ is an aryl group, a heterocyclic group or an aryloxy group, thearyl group, the heterocyclic group or the aryloxy group optionally hasone or a plurality of substituents selected from the group consisting ofa halogen atom, a lower alkyl group, a halogenated lower alkyl group, anaryl group, a hydroxy group, a lower alkoxy group, a halogenated loweralkoxy group, a lower alkylthio group, a lower alkylcarbonyl group, alower alkoxycarbonyl group, a lower alkylcarbonyloxy group,—NR^(a)R^(b), a nitro group and a cyano group; R^(a) and R^(b) are thesame or different and represent a hydrogen atom, a lower alkyl group ora lower alkoxycarbonyl group; R⁸ represents a hydrogen atom or a loweralkyl group; in the case where R⁸ is a lower alkyl group, the loweralkyl group optionally has one or a plurality of substituents selectedfrom the group consisting of an aryl group or a heterocyclic group; Yrepresents a lower alkylene group; Z represents an oxygen atom; prepresents 0, 1 or 2, in the case where p is 2, each R⁶ is the same ordifferent.
 5. The method according to claim 1, wherein in the formula(1), R¹ represents a lower alkyl group; R² represents a hydrogen atom;R³ and R⁴ represent a lower alkyl group; R⁵ represents a lower alkylgroup; R⁶ represents a halogen atom, a lower alkyl group, a hydroxygroup, a lower alkoxy group or a nitro group; X represents —CO—,—C(O)NR⁸— or —S(O)₂—; R⁷ represents a lower alkyl group, a lower alkenylgroup, a lower cycloalkyl group, an aryl group, a heterocyclic group, alower alkoxy group or an aryloxy group; in the case where R⁷ is a loweralkyl group, the lower alkyl group optionally has one or a plurality ofsubstituents selected from the group consisting of a halogen atom, anaryl group, a heterocyclic group, a lower alkoxy group and —NR^(a)R^(b);in the case where R⁷ is an aryl group, the aryl group optionally has oneor a plurality of substituents selected from the group consisting of ahalogen atom, a lower alkyl group, a halogenated lower alkyl group, alower alkoxy group, a halogenated lower alkoxy group, a lower alkylthiogroup, a lower alkylcarbonyl group, a lower alkoxycarbonyl group, alower alkylcarbonyloxy group, —NR^(a)R^(b), a nitro group and a cyanogroup; in the case where R⁷ is a heterocyclic group, the heterocyclicgroup optionally has one or a plurality of substituents selected fromthe group consisting of a halogen atom, a lower alkyl group, an arylgroup, a hydroxy group, a lower alkoxy group, a lower alkylthio group, alower alkylcarbonyl group, a lower alkoxycarbonyl group and a nitrogroup; in the case where R⁷ is a lower alkoxy group, the lower alkoxygroup optionally has one or a plurality of substituents selected fromthe group consisting of a halogen atom and an aryl group; in the casewhere R⁷ is an aryloxy group, the aryloxy group optionally has one or aplurality of substituents selected from the group consisting of ahalogen atom and a lower alkoxy group; R^(a) and R^(b) are the same ordifferent and represent a hydrogen atom, a lower alkyl group or a loweralkoxycarbonyl group; R⁸ represents a hydrogen atom or a lower alkylgroup; in the case where R⁸ is a lower alkyl group, the lower alkylgroup optionally has one or a plurality of substituents selected fromthe group consisting of an aryl group or a heterocyclic group; Yrepresents a lower alkylene group; Z represents an oxygen atom; prepresents 0, 1 or 2, in the case where p is 2, each R⁶ is the same ordifferent.
 6. The method according to claim 1, wherein in the formula(1), Z represents an oxygen atom.
 7. The method according to claim 1,wherein in the formula (1), R¹, R³, R⁴ and R⁵ represent a methyl group;R² represents a hydrogen atom; and Y represents a methylene group. 8.The method according to claim 1, wherein the compound is selected fromthe group consisting of6-(4-benzoyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-(4-t-butoxycarbonylaminoacetoxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-methoxybenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3-methoxybenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-methoxybenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,6-[4-(2-chlorobenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-(4-cyclohexylcarbonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(pyridin-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,6-(4-butyryloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-(2-methoxy-4-propionyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-(4-acryloyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(thiophen-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[4-(furan-2-ylcarbonyloxy)-2-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-(4-isobutyryloxy-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline,(5-fluoro-2-methylphenoxymethyl)-6-(2-methoxy-4-phenylacetoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-(2-methoxy-5-propionyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(thiophen-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3-phenylpropionyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[4-(furan-3-ylcarbonyloxy)-2-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(pyridin-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-nitrobenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(pyridin-4-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-5-(pyridin-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-5-(pyridin-4-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,6-[4-(2-acetoxybenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-[4-(1-t-butoxycarbonylpiperidin-4-ylcarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-methylthiobenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,6-[4-(1-t-butoxycarbonylimidazol-4-ylcarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(thiazol-4-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(thiazol-5-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(oxazol-4-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,6-[4-(3-acetylbenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-[4-(2-fluorobenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-[4-(3-fluorobenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(5-methylfuran-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-methylpyridin-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(pyridin-3-ylacetoxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,6-[4-(4-acetylbenzoyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3-methoxycarbonylbenzoyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(6-methylpyridin-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-methylpyridin-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3-methylfuran-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,6-(4-t-butylcarbonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(pyrimidin-5-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(5-nitrofuran-2-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,6-[4-(2-chloropyridin-4-ylcarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[4-(3-fluoropyridin-4-ylcarbonyloxy)-2-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,6-[2-methoxy-4-(2-methoxybenzoyloxy)phenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-[2-methoxy-4-(pyridin-3-ylcarbonyloxy)phenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-[4-(furan-2-ylcarbonyloxy)-2-methoxyphenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-[4-(2-chlorobenzoyloxy)-2-methoxyphenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-[2-methoxy-4-(2-methylpyridin-3-ylcarbonyloxy)phenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-[2-methoxy-4-(2-methoxybenzoyloxy)phenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(2-methoxy-5-nitrophenoxymethyl)-6-[2-methoxy-4-(thiophen-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,6-[4-(furan-3-ylcarbonyloxy)-2-methoxyphenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-[2-methoxy-4-(2-methylpyridin-3-ylcarbonyloxy)phenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-methoxypyridin-3-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,6-(4-aminoacetoxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-(2-methoxy-4-propylsulfonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-(4-ethylsulfonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-(4-isopropylsulfonyloxy-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-(4-butylsulfonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(2-methoxy-5-nitrophenoxymethyl)-6-(2-methoxy-4-propylsulfonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-(4-cyclopropylsulfonyloxy-2-methoxyphenyl)-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-(4-isopropylsulfonyloxy-2-methoxyphenyl)-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-(4-ethylsulfonyloxy-2-methoxyphenyl)-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-(2-methoxy-4-propylsulfonyloxyphenyl)-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-(4-isopropylsulfonyloxy-2-methoxyphenyl)-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-(4-cyclopropylsulfonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-(4-isobutylsulfonyloxy-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-(4-cyclopentylsulfonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3,3,3-trifluoropropylsulfonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(2-methoxyphenoxycarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,6-[4-(2-chlorophenylaminocarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(3-methoxyphenylaminocarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-methoxyphenylaminocarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(4-methoxycarbonylphenylaminocarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,6-(4-dimethylaminocarbonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-[4-(4-cyanophenylaminocarbonyloxy)-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,5-(5-fluoro-2-methylphenoxymethyl)-6-[2-methoxy-4-(morpholin-4-ylcarbonyloxy)phenyl]-2,2,4-trimethyl-1,2-dihydroquinoline,6-(4-isopropylaminocarbonyloxy-2-methoxyphenyl)-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-[2-methoxy-4-(morpholin-4-ylcarbonyloxy)phenyl]-5-(2-methoxy-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-[2-methoxy-4-(morpholin-4-ylcarbonyloxy)phenyl]-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-(4-dimethylaminocarbonyloxy-2-methoxyphenyl)-5-(2-methyl-5-nitrophenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-[4-[N-benzyl-N-(2-dimethylaminoethyl)aminocarbonyloxy]-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,6-[4-[N-(2-dimethylaminoethyl)-N-(pyridin-3-ylmethyl)aminocarbonyloxy]-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,and6-[4-[N-(2-dimethylaminoethyl)-N-ethylaminocarbonyloxy]-2-methoxyphenyl]-5-(5-fluoro-2-methylphenoxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline,or a pharmaceutically acceptable salt thereof.
 9. The method accordingto claim 1, wherein the glucocorticoid receptor-related disease isglaucoma.